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2.1.1.8.1 Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reactions

DOI: 10.1055/sos-SD-205-00001

Nagasawa, K.; Sohtome, Y.Science of Synthesis: Asymmetric Organocatalysis, (2012233.

Catalytic enantioselective inverse-electron-demand hetero-DielsAlder reactions (IEDDA) of chalcones with oxazol-5(4H)-ones (azlactones) employing the C2-symmetric chiral bisguanidine 87 have been developed by Feng and co-workers. In these processes, chiral γ,δ-unsaturated δ-lactones 88 with a quaternary stereogenic center are generated.[‌46‌]

Meeeeee-eeeeeeee-eeeeee eeeeee-MeeeeMeeee eeeeeeeee ee eeeeeeee eeeeeeeeeee 88 eeeeeee eeee eeeeeeee-eeeeeeeeeee eee eeeeeeee-eeeeeeee eeeeee ee eeee ee eeeeeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeee eeee e eeeeeee ee eeeeee-8(8M)-eeee 88 eeeeeeeee ee 88 ee eeeeeee eee eeeeeeeeeeeee eeeeeee 88 ee eeeeeeee ee eeee eeeeee (8888%) eee eeee eeeeeeeee eeeeee ee eeeeeeeeeeeeeeeeee (8888% ee) (Meeeee 88). Meeee eeeeeee ee Meeeeee eeeeeee 88 eee eeee eeeeee ee eeeee eeeeeeeee. Meee eeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeeeee (8888% ee) eee eeeeeeee eeeeeeeeee ee eee eeeeeeeeee eee eeeeee eeeeee ee eee M8 eeeeeeeeeee ee 88. Meeeeeee, eeeee eeeeeeeee eee ee eeeeeee eee ee eeee eeeeee eee eee eeeeeeee eee ee eeeeeeeee eee eeeeee eeeeeee eeee ee eeeeeeee ee eeeeeeeeeeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeee Meeeee-MeeeeMeeee Meeeeeeee ee Meeeee eee Meeeee-8(8M)-eeee Meeee e Meeeee Meeeeeeeeeee Meeeeeee[‌88‌]

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Me8 M8 M8 M8 Meee (e) Meeee (%) ee 88 ee (%) ee 88 Mee
Me Me Me Me 88 88 88 [‌88‌]
8-MeM8M8 Me Me Me 88 88 88 [‌88‌]
8-MeM8M8 Me Me Me 88 88 88 [‌88‌]
8-MeM8M8 Me Me Me 88 88 88 [‌88‌]
8,8-Me8M8M8 Me Me Me 88 88 88 [‌88‌]
8-MM8M8 Me Me Me 88 88 88 [‌88‌]
8-MeM8M8 Me Me Me 88 88 88 [‌88‌]
8-MeM8M8 Me Me Me 88 88 88 [‌88‌]
8-Mee Me Me Me 88 88 88 [‌88‌]
8-Mee Me Me Me 88 88 88 [‌88‌]
8-MeMM8M8 Me Me Me 88 88 88 [‌88‌]
8-MeM8M8 Me Me Me 88 88 88 [‌88‌]
8-eeeeeeee Me Me Me 88 88 88 [‌88‌]
8-eeeeeeee Me Me Me 88 88 88 [‌88‌]
Me Me Me 88 88 88 [‌88‌]
8-eeeeeee Me Me Me 88 88 88 [‌88‌]
Me 8-MM8M8 Me Me 88 88 88 [‌88‌]
Me 8-MeM8M8 Me Me 88 88 88 [‌88‌]
Me 8-Mee Me Me 88 88 88 [‌88‌]
Me 8-Mee Me Me 88 88 88 [‌88‌]
Me 8-eeeeeeee Me Me 88 88 88 [‌88‌]
Me Me Me 88 88 88 [‌88‌]
Me MM8MM=MMMe Me Me 88 88 88 [‌88‌]
Me 8-eeeee Me Me 88 88 88 [‌88‌]
Me 8-eeeeeee Me Me 88 88 88 [‌88‌]
Me Me 8-MeM8M8 Me 88 88 88 [‌88‌]
Me Me 8-MeM8M8 Me 88 88 88 [‌88‌]
Me Me 8-MeM8M8 Me 88 88 88 [‌88‌]
Me Me 8-Mee Me 88 88 88 [‌88‌]
Me Me 8-MeMM8M8 Me 88 88 88 [‌88‌]
Me Me Me Me 88 88 88 [‌88‌]
Me Me Me (MM8)8MMe 88 88 88 [‌88‌]
Me Me Me Me 88 88 88e [‌88‌]
Me Me Me Me 88 88 88e [‌88‌]

e Meeeeeee eeeeeee eee ee e 8-eeee eeeee.

e Mee eeeeeeee eee eeeeeeeee ee 88% eeeee eee eeeeee ee e 8.88-eeee eeeee.

Meeeeeeeeeee Meeeeeeee

M-[(8M,8M)-8-Meeeee-8-eee-8,8-eeeeeeee-8,8-eeeeeee-8M-eeeee-8-ee]eeeeeeeee (88, Me8=M8=M8=Me; M8=Me); Meeeeee Meeeeeeee eeee Meeeeeee Meeeeeee:[‌88‌]

Me e eeeeeee eeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (88, Me8=M8=Me; 8.88e, 88eeee, 8 eeeee) eee eeeeeeeee 88 (888ee, 8.8eeee, 88eee%) ee MMM/MMMe8 (8:8; 88eM) eee eeeee eeeeee eeeeee-8(8M)-eee 88 (M8=Me; M8=Me; 8.888e, 8eeee, ee eeeeeeee) ee MMM/MMMe8 (8:8; 88eM) ee 88°M. Meeee eeeee eeeeeee eee 88e, eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee) ee eeeeee eee eeeee eeeeeee (eeeeee eeee eeeeeeeee eeeee/MeMMe 8:8) eee eeeee eeeeeeeee eeeeeeeee 88 (eeeeee eeee MeMM/MeMMe 8:8 ee 8:8). Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8 ee 88:8) ee eeeeee eee eeeeeee ee 88 eee Meeeeee eeeeeee 88, eeeeeeee ee e eeeeee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeeeeee eeeee 8:8 ee 8:8) ee eeee eeee eeeeee 88 (Me8=M8=M8=Me; M8=Me); eeeee: 8.888e (88%, ee eeeeeeee).

Me e eeee ee eee eeeee eeeeeeeee eeeeeeeee 88 ee MM8Me8 (88eM) eee eeeee 8M MeMM (88eM). Mee eeeeeeeee eeeeeee eee eeeeeee eeeee ee eeeeee eeeee (eM8888) eee eee eeee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee 8M MeMM, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eeee 88 ee e eeeee eeeee: eeeee: 888ee (88%).

References