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2.4.1.1 Diastereoselective (3 + 2)-Cycloaddition Reactions of Carbonyl Ylides with Carbon–Carbon π-Bonds

DOI: 10.1055/sos-SD-222-00100

Xu, X.; Hu, W.Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (20162170.

The intramolecular cycloaddition reaction of carbonyl ylides with alkenes, alkynes, and allenes is an effective method for the construction of polycyclic and endocyclic structures.[‌16‌‌19‌]

Meeeee ee eee eeeeeee eeeeeee eee eee eeeeeeeee eeeeeeeeeeeee eeeeeeeee ee α-eeeee-β,ε-eeeee eeeeee; eeeeeee, eee eeeeee eeeeeee eeeeeeeee 88 ee eeeeeeeee ee eeeeee, eee eeeeeee ee eeee ee eeee eeeeeeee eeeeeeeeee. Meeeeeee ee eeeeee eeeeeee 88 eeeeeeeee ee eeeeeee(MM) eeeeeee eeeee [Me8(MMe)8; 8, M8 = Me] eeeee eeeeeeeeeee 88 ee 88% eeeee, eeeeeee eee eeee eeeeeeee-eeeeeeeee eeeeeee(MM) eeeeeeeeeeeeeeee eeeee [Me8(eee)8; 8, M8 = MM8] eeeee 88 ee ee eeeeeeee 88% eeeee. Me eeeeeeee, Me8(eee)8 (8) eeeee ee eeeeeeeee eeeeee eeeeeee eeeeeeeee 88, eeee eeeee 88 eeeee. Mee eeeeeee(MM) eeeeeeeee eeeee [Me8(Mee)8; 8, M8 = (MM8)8Me], eeeee ee eeeeeeeeeeeeee eeee eeeeeee ee eeeeeee(MM) eeeeeee eeeee eee eee eeeeee eeeeeeeeee ee eeeeeeee eeeeeeee, eeeee eeeeeeeeeee 88 ee 88% eeeee (Meeeee 8). Meeeeeeeee eeeeeeeee eeeee eeeeeee eeeeee eeeeeeeee eeeeeeeee eeeee eeee eeeeeeee eeeeeeeeeeeeeeeeee.[‌88‌]

Meeeee 8 Me Meeeeeeee-8M-8e,8-eeeeeeeeeee-8-eee ee Meeeeee-Meeeeeeee Meeeeeeeeeeeeeeeee Meeeeeeeeeeeee (8 + 8)-Meeeeeeeeeeee Meeeeeee ee e Meeeeeee Meeee eeee ee Meeeee[‌88‌]

8-Meeeeeeeeeee-8,8-eeeee (88) eeeeeeeee eeeeeee(MM) eeeeeee eeeee eeeeeeeee eeeeee eeeeeeee eeeee eeeeeeeee–eeeeeeeeeeeee eeee eeeeeeeee eeeeeee ee eeee eeeeeeeeeee 88 ee 88% eeeee (Meeeee 8). Meee eeeeeeeeeeeee eeeee eeee eeeee- eee eeeeeeeeeeeeeeee; eee eeeeeeeeeeeeeeee eee eeeeeeeeee ee MMM eeeeeee. Meeeeee 88 ee e eeeeee, eeeeeee eeeeeeeeeeee ee eee eeeeeeeee ee eee-eeeeeeeeee eeeee.[‌88‌]

8-Meeeeeeeeee-8,8-eeeee (88) eeeeeeeee e eeeeeee eeeeeeee eeee eee eeeeeeeeee-eeeeeeeee eeeeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee. Mee eeeeee eeeeeeee eeeee eeeeeeeee–eeeeeeeeeeeee eeeeeeee ee eeeeeeeee ee e eeeeeeeeee eeeeeeeee(MM) eeeeeeeee eeeeeeee (8 eee%) eeee 88 eeeee ee eeee eeeeeeeeeee ee eeeeee 88 ee 88% eeeee eeee e MMM ee 888.[‌88‌]

Meeeee 8 8-Meeeeeeeee[8.8.8]eee-8-ee-8-eeee ee Meeeeeeeeeeeeeeeee Meeeeeeeeeeeee (8 + 8)-Meeeeeeeeeeee Meeeeeee ee Meeeeeee Meeeee eeee Meeeeee[‌88‌,‌88‌]

Meee eeeeeeee eee eeeeeeeeeee eeeeeee eee eeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeeee eeeeee eeee eeeeeee. Meee eee ee eee eeeeeeee eeeeeeeeeeeee eee eeeeee (Meeeee 8), eee eee eeeeeeee eeeeee ee eeeeeeeeeeeeeeeeeeee eee eeeeeeee (8.8:8 ee 8.8:8). Me eeeeeee, eee eeee ee eee M8 eeeee ee 88 eeeeeee ee eeee e eeeeeeeeee eeeee eeeeee ee eee eeeeeeeeeeeeeeeeeeee.[‌88‌]

Meeeee 8 8-Meeeeeeee-8-eeeeeeeeee[8.8.8]eeeee-8-eeee ee Meeeeee-Meeeeeeee Meeeeeeeeeeeee (8 + 8)-Meeeeeeeeeeee Meeeeeee ee Meeeeeee Meeeee eeee Meee-8,8-eeeeeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 M8 Meeeee (eeee/eee) Meeeee (%) ee 88 Mee
Me M Me 88:88 88e [‌88‌]
Me Me Me 88:88 88 [‌88‌]
Me Me Me >88:88 88e [‌88‌]
Me M Me 88:88 88e [‌88‌]
Me Me Me >88:88 88e [‌88‌]
e-Me M Me 88:88 88 [‌88‌]
e-Me Me Me 88:88 88 [‌88‌]
e-Me Me Me >88:88 88e [‌88‌]
e-Me Me Me 88:88 88 [‌88‌]
e-Me Me Me 88:88 88 [‌88‌]
e-Me Me Me >88:88 88e [‌88‌]
e-Me eMe Me 88:88 88e [‌88‌]

e Meeeeeeeee ee 8M MMM eeeeeeeeeeee ee eee eeeee eeeeeeee eeeeeee.

e Meeeeeee eeeeeeee eeeee ee eeeeeeee.

e Meeeeeee eeeee ee eeeee eeeeeee eeee-88.

Mee eeeeeeeeeeeeee (8 + 8) eeeeeeeeeeeee ee e eeeeeeee eeeee ee ee eeeeee ee e eeeee-eeeeeeeee eeeeeeee eeeeeeeee eeeee eeeeeeeee, eeeeeeeee (ee eeeeeee), eee eeeeeee ee eeee eeeeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeeeee eeee eeeeeeeee eeeeeeeee (Meeeee 8).[‌88‌,‌88‌] Meeeeeee eeeee eeeeee, eee eeeeeee e eeeeeeeee eeeeeeee,[‌88‌] eee ee eeee, eeeeeeeee eeeeeeeeeee eeeeeeeee eee eee eeeeeeee ee eeeeee; eee eeeeeeeeeeeeeeeeeeee eeeeeee eeeeee eeeeeee ee eee eeeeee eee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeee.[‌88‌,‌88‌] Meeeeeeeeee eeeeeeeee ee e eeeeeeeee/Meeee eeee eeeeee ee eeeeeeeeeee ee eee eeeeeee (Meeeee 8); eeee eeee eeeeeeeeeeeeeeeeeeee ee eeeeeeee eee eee eeeeeeeeeeeee (8 + 8)-eeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeeeee eeee eeeeeee eeee eeee e eeeee-ee eeeeeeeeeeee eeee.[‌88‌]

Me eee eeeeeeeeeeeeee (8 + 8) eeeeeeeeeeeee ee e eeeeeeee eeeee ee ee eeeeee, eeeeeeee ee eee eeeeeeeeeeeeee eeeeeee, eeeeeeeeeee eeeeeeeee, eeeeeeeee eeeeeeeeeee eee eeeeeeeeeeeee eeee e eeeeeee eeeeeeeeee ee eeeeeeee, eee eee eeee eeeeee; eee eeeeeeeeeeeeeeee eeeeee eeeeeee ee eee eeeeee eee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeee.[‌88‌] Meeee 8-eeeee-8M-eeeeee-8,8(8M)-eeeee (88) ee eee eeeee–eeeeeee eeeeeeeee ee eeee eeeee-eeeeeeeee eeeeeeee eeee eeeeeeeee eee M-eeeeeeeeeeeeee 88 eeeee eeee eeeeee ee eeeeeeeeeee eeeeeeee 88 (Meeeee 8).[‌88‌] Mee eeeeeeeeee eeeeeee ee eeeeeeeeeeee eeee ee eee M-eeeeeeeeeeeee eee eee eeeeeeee eeeeeeee eeee eeeeee eeeeeeeee ee eee eeeeeeeeeeeeeeeeeeee, eee eeeeeeeeeeee eeeeee eee eeeeeeee ee eeee eeeee. Mee eeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee ee eee eeeeeeee eeeeeeeee eee eeee eeee eeeeeee ee eeeee-eeeeeee eeeeeeeeeeeeeee eeeeeeee 88 ee eeeeeeee eeeeee.[‌88‌]

Meeeee 8 Meeee-Meeee Meeeeeeeeee ee Meeeeee-Meeeeeeee Meeeeeeeeeeeeeeeee Meeeeeeeeeeeee (8 + 8)-Meeeeeeeeeeee Meeeeeee ee ee Meeeee-Meeee Meeeeeee Meeee eeee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Meeeee (eeee/eee) Meeeee (%) Mee
Me Me 88:88 88 [‌88‌]
Me Me 88:88 88 [‌88‌]
Me 8-M8MM8M8 88:88 88 [‌88‌]
Me 8-MeMM8M8 88:88 88 [‌88‌]
Me 8-MeM8M8 88:88 88 [‌88‌]
Me 8,8-Me8M8M8 88:88 88 [‌88‌]
8-MeMM8M8 8,8-Me8M8M8 88:88 88 [‌88‌]
8-M8MM8M8 8,8-Me8M8M8 88:88 88 [‌88‌]
8,8-Me8M8M8 88:88 88 [‌88‌]
88:88 88 [‌88‌]
(M)-MM=MMMe 8,8-Me8M8M8 88:88 88 [‌88‌]
(M)-MM=MMMe 8-MeM8M8 88:88 88 [‌88‌]

e Meeeeeeeee ee 8M MMM eeeeeeeeeeee ee eee eeeee eeeeeeee eeeeeee.

e Meeeeeee eeeeeeee eeeee ee eeeeeeee.

Me eeeeeeeee eeeeeeee ee eeeeeeee eee eeeeeeee eeee eeeeeeeee ee eeeee eeeee-eeeeeeeee eeeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee. Meeeeeeeeee eeeeeeeee, eeeee e eeeeee eeeeeeee ee eeeeeeee eee eeeeeeeeeeeee 88, eee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeee eee eeee eee eeeeeee eeeeeeee 88 ee eeee eeeeee (88–88%) eeee eeeeeeeee eeeeeeeeeeeee (ee ee ee 88:8) eee eee eeeeeee eeeeeeeeee eeeee eeeee ee Meeeee 8.[‌88‌]

Meeeee 8 Meeeeeeeeee Meeeeee/Meeeee-Meeeeeeee Meeeeeeeeeeeeeeeee Meeeeeeeeeeeee (8 + 8)-Meeeeeeeeeeee Meeeeeee ee Meeeeeee Meeeee eeee Meeeeeeeeeeeeeee Meee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 M8 M8 eee Meeeee (%) Mee
Me Me Me Me 88:8 88 [‌88‌]
Me Me Me Me 88:8 88 [‌88‌]
Me Me Me Me 88:8 88 [‌88‌]
Me Me Me Me 88:8 88 [‌88‌]
8-Mee Me Me Me 88:8 88 [‌88‌]
8-MeM8M8 Me Me Me 88:8 88 [‌88‌]
8-M8MM8M8 Me Me Me 88:8 88 [‌88‌]
Me Me Me Me 88:8 88 [‌88‌]
Me Me Me Me 88:8 88 [‌88‌]
Me Me Me Me 88:8 88 [‌88‌]
Me Me e-Me Me 88:8 88 [‌88‌]

e Meeeeeeeeeeeee eeeee eee eeeeeeeeee ee 8M MMM eeeeeeeeeeee.

e Meeeeeee eeeeeeee eeeee ee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

8-(Meeeeeeeeeeeee)-88-eeeeeeeeeee[8.8.8.88,8]eeeeeee-8-eee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee 8-eeeee-8-(eeeeeeeeeeeeee)eee-8-eee-8,8-eeeee (88; 88 ee, 8.8 eeee) ee eeeeeee (8.8 eM). Me8(Mee)8 (8.8 eee%) eee eeeee ee ee eee eee eeeeeee eee eeeeeee eeeee eee eeeeeeeee eee eeee eeeeeeee [eeeeeeeee eeeeee 8 e, MMM eeeeeeeeee (eeeeeeeee eeeee/Me8M 8:8; Me 8.8)]. Mee eeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/Me8M 8:8) ee eeee eeee eeeeeee ee eeeee eeeeeeee; eeeee: 88 ee (88%); ee 888–888 °M.

Meeeeeee 8-Meeeee-8-eee-8-eeeeeeeeee[8.8.8]eee-8-eee-8,8-eeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee MMMM (88 ee, 8.88 eeee) eee eeeeeeee(8,88,88,88-eeeeeeeeeeeeeeeeeeeeeee)eeeeeeeee(MM) (8.8 ee, 8.888 eeee) ee MM8Me8 (8.8 eM). M eeee ee 8-eeeeeeeeeee-8,8-eeeee (88; 88 ee, 8.8 eeee) eee eeeee eeeeeeee ee ee eeee 8 e eeeee e eeeeeee eeee. Meeee eee eeeeeeeee eee eeee eeeeeeee [MMM eeeeeeeeee, (eeeeeee/MeMMe 8:8; Me 8.8)], eee eeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee/MeMMe 8:8) ee eeee eeee eeeeeee ee eeeeeeeee eeeeeeee; eeeee: 88 ee (88%); ee 88–88 °M.

Meeeeee 8-Meeeeeeeee-8-eeeeee-8-eee-8-eeeeeeeeee[8.8.8]eeeeee-8,8-eeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee eeee-8,8-eeeeeeee 88 (8.8 eeee) eee 8,8-eeeeeeeeeeeeee (8.8 eM). Me eeee eeee eee eeeee e eeee ee Me8(MMe)8 (8.8 ee, 8.888 eeee, 8.8 eee%) ee 8,8-eeeeeeeeeeeeee (8.8 eM). Mee eeeeeee eee eeeeee ee 88 °M eee 88 (8.8 eeee) eee eeeee ee e eeee ee 8,8-eeeeeeeeeeeeee (8.8 eM), eeeeeeee ee eeeeeee (888 µM) (MMMMMMM: eeeeeeeeee). Mee eeeeeee eee eeeeeee ee 88 °M eee 88 e (MMM eeeeeeeeee). Meee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee/MeMMe 88:88) ee eeee eee eeee eeeeeee.

8,8-Meeeee-8e,8e-eeeeeeeeeeee[eeee[8,8-e]eeeeeee-8,8′-eeeeee]-8′,8′,8,8(8M,8M)-eeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee 8-eeeee-8M-eeeeee-8,8(8M)-eeeee (88; 8.8 eeee), eeeeeeee (8.8 eeee), M-eeeeeeeeeeeee 88 (8.8 eeee), Me8(MMe)8 (8.8 ee, 8.88 eeee), eee 8-Å eeeeeeeee eeeeee (8.8 e) ee 8,8-eeeeeeeeeeeeee (88 eM), eee eee eeeeeee eee eeeeeee ee 88 °M eee 8–8 e eeeee ee eeeee eeeeeeeeee. Meee, eee eeeeeee eee eeeeeeee eeeeeee Meeeee, eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8 ee 8:8) ee eeee eee eeee eeeeeee.

Meeee 8-Meeeee-8-[(M)-8-eeeeeeeee-8-eeeeeeeeeeeeee-8-eeeeeeee]-8-eeeeee-8-eeeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeee (88, M8 = Me; M8 = Me; M8 = Me; M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee (M)-8-[(M)-eee-8-eeeee]-8-eeeeeeeeeeeeeeeeeee-8-eee (88, M8 = Me; 88.8 ee, 8.88 eeee), Me8(MMMe-Me)8 (8.888 eeee), Me(MM8)8•8M8M (8.888 eeee), eee 8-Å eeeeeeeee eeeeee (888 ee) ee MM8Me8 (8.8 eM) ee −88 °M (eee eee/eeeeeee eeee). M eeee ee eeeee 8-eeeee-8-eeeeeeeeeeeeeeee (88, M8 = Me; M8 = Me; 8.88 eeee) eee eeeeeeeeeeee (8.88 eeee) ee MM8Me8 (8.8 eM) eee eeeee ee eee eeeeeee eeee e eeeeee ee 8 e eeeee e eeeeeee eeee. Mee eeeeeee eee eeeeee eeee MM8Me8 (8.8 eM), eee eeee eeeeeeee eee eeeeeeeee eee 88 eee ee −88 °M. Mee eeeeeee eee eeeeee ee ee, eee eeee ee eee eeeeeeee eeeeeee Meeeee (8 ee) eee e eeee ee eeeeee eee (8 ee), eeeeeee eeee eeeeeee/MeMMe (8:8; 88 eM). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee/MeMMe 88:8 ee 88:8) ee eeeeeee eeee eeeeeee ee e eeeeeeeee eeeee; eeeee: 888.8 ee (88%); ee 888–888 °M.

References