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DOI: 10.1055/sos-SD-219-00174

Wang, S.-H.; Tu, Y.-Q.; Tang, M.Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (20151344.

Other than the two major reaction types outlined in Sections and, a domino process involving a ring closure can also be initiated by a nucleophilic step, which is normally induced by a Lewis basic reagent.

Me 8888, Meeeeeeeʼe eeeee eeeeeeee e eeeeeee eeeeeeeee ee (+)-eeeeeeeeeeee,[‌888‌] ee MMM-8 Mee/Mee-eeeeeeeeee eeeeeee eeeeeeeee eeee e eeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee. Meeeee eeeee eeeee, e 8,8-eeeeeeeeeeee[8.8.8]eeeeee-eeeeeeeee eeeeee eeeeeeeeeee eee eeee ee eee eee eeee eee eee eeeeeeeeeeee ee eee eeeeeee eeeeeeee eeeeee. Mee ee eee eeeeeeeee ee eeeeeeee eeeeeeee eeeee eee eee eeeeeee eeeeeeee eeee, eee eeeeeeeeeee ee eeee e eeeeeeee eee eeeeeeeee eeeeee ee e eeeee eeeee ee eee eee eeeeeeee eeeeeeee (Meeeee 88). Meeeeeeeeee, eeeeeeeeee 888 eee 888 eee eeeeeee eeee 8,8-eeeeeeeeeeee[8.8.8]eeeeee, eee eeee eeeeee eeeeeeee eee eee Meeeee–Meeeee–Meeeeee eeeeeeee, eee eeeeee eee eeeeeee eeeeeeee 888 eee 888, eeeeeeeeeeee. Meeeeeeeeeeee, eee eeeeeeee ee eee eeeeeeeeeee 8,8-eeee eeeeee ee eeeeeeeee 888 eeeeeeeeeeeee eeeeeeeeeee eee eeeeee eeeeeeee.

Meeeee 88 8,8-Meeeeeeeeeee[8.8.8]eeeeee-Meeeeeeee Meeeee Meeeeeeeeee[‌888‌]

Meeeeeee eeee eeeeee, eee eeeee eeeeeeeee ee (+)-eeeeeeeeeeee ee eeeeeeeeeeee eeeeeee eee eeeeeeeeeee ee eee eeee eeeeeee eeeeeeeee 888, eeeee ee eeeeeeee eeee eeeeeeeeeeee eeeeeeeee 8-eeeeeeeeeeeeeee-8-ee-8-eee ee 88 eeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeee Meeeeeeee ee (+)-Meeeeeeeeeee[‌888‌]

Meeeee eeeeeeeee eeeeee eee eeeeeee eeee ee Meeee eeee eeeeeeee eeee eee eeee eeeeeee ee eeee eeeeee eeeeeeeee eee eeee eeeeeeeeee ee eeee ee eee eeeeeee eeeeeeeeeeeeeee eeeee. Me eeee eeeeeeeeeeeeee eeeeeee eeeeeeee eeeeeee eeeeeee eee/ee eeeeeee eeeeeeeeee, ee eee eeee eeee eeeeee ee eeeeeee eeeeeeeee ee eeeeeee eeeeeeeee.[‌888‌‌888‌]

Mee eeeeeee, MeeMeeeee eee ee-eeeeeee eeee eeeeeeeee ee eeeee-eeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeee eeeeeeee–eeeeeeeeeee eeeeeeee ee eeee eeeeeeeeeeeeeeee[8,8-e]eeeeeee 888 (Meeeee 88),[‌888‌] eeeee eee eee eee eeeeeeeeee eeeee ee eeee eeeeeeeee eeeeeeeeeeee eeeeeeeee. Me eee eeee eeeeeeee eeeeeeeeee, eeeeeeeee eeeeeeeeeeee ee eee eeeee eee ee-eeeeeeee eeeeee eee eeeeeee ee eee eeeeeeeeeeeeee. Meee, eee eee ee e eeeeeeeeee-eeeeeee eeeeeeee 888 eeeee eee eeee eeeeeeeeeee. Meeeeeeeeeeee, eee eeeeeeeeee eeeeeeee ee eee eeeeeee eee eeee eeee ee eeeeeee ee eeeeeeeeeeeeeeeeee. Meee eeeeeeee eeee eeeee eeeee eeeeeeeee eeeee. Meeeeee, eeeeeeeeee 888 eeee eeeeeeeee M8 eee M88 eeeeeeeeeeee (M8 eee M8) eee eeee eee eeeeeee eeeeeee eeee eeeeeeeee eeeee eee eeeeeeeeeeee eeeeee. Meeeeeee, eee eeeeeeee ee eeeeeeee ee eeeeeeeee ee eee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeee ee eee eeeeee eeee (M8 eee M8). Meeeeee, eee eee eeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeee ee eee 8-eeeeeeee (M8), eeee eeeeeeeee eeeeeeee eee eeeeeeee eeeeeeeeeeeee eee ee eeeeeeee, eeeeee ee eee eeeeeeeeeeeeeee. Meeeeeeeeee, eee eeeeeeeeeeeee eeeeeeeeee-8M-eeee[8,8-e]eeeeee eeeeeeee 888 eee ee eeeeeeeeeee ee eee eee ee e eeeeeeeeee eeeeeeeeee (Meeeee 88).

Meeeee 88 Meeee-Meeeeeeee Meeeeeeeeeeeeeee Meeeeeeeee Meeeeeee–Meeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Me8 MM Meeeeeeeee ee (%) Meeee (%) Mee
M M MM8MM=MM8 Mee M Me MMM MM8Me8/M8M, −88 °M 88 88 [‌888‌]
M M MM8MM=MM8 Mee M Me MMe eeeeeee/M8M, 8 °M 88 88 [‌888‌]
M M MM8MM=MM8 Mee M eeeee-8-ee MMM MM8Me8/M8M, −88 °M 88 88 [‌888‌]
M M MM8MM=MM8 MM8Me M eeeee-8-ee MMM MM8Me8/M8M, −88 °M 88 88 [‌888‌]
M M Me Mee M eeeee-8-ee MMM MM8Me8/M8M, −88 °M 88 88 [‌888‌]
M M MM8MM=MM8 Mee MM8MMe Me MMM MM8Me8, −88 °M 88 88e [‌888‌]
M Me MM8MM=MM8 Mee MM8Me Me MMM MM8Me8, −88 °M 88 88e [‌888‌]
Me M MM8MM=MM8 Mee MM8Me Me MMM MM8Me8, −88 °M 88 88e [‌888‌]

e ee 88:8.

e ee 88:8.

e ee 88:8.

Mee eeeeeeeee eeeeeee ee eeee eeeeee eee eeee eeee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee (−)-eeeeeeeeeee M (Meeeee 88).[‌888‌]

Meeeee 88 Meeee Meeeeeeee ee (−)-Meeeeeeeeee M[‌888‌]

Meeeeee eee eeeeee eee ee eee eeeeeeeeee eeeee, eeeeeeee eeeeee eeeeeeeeeeeeeee eeee eeee eeeeeeeee eeeeeee eee eeeeeeeeeee ee eeeee eee eeeeeeeeee eeeee eeee eee eeeeee ee eeeeeeeeee eeee eeeeeeeee eeeeeeee eeeee. Meeee eeeeeeeeeeeeeee eee ee eeee eeeeeee ee eee eeeee eeeeeeeee ee eeeeeee eeeeeeee eee, eeeee eeeee eeeeeeee eeeeeeee, eee eeeeeee–eeeeeee eeeeeeee ee eee ee eee eeee eeeeeeee eeeeeee.

Me eeeeee eee eeee eeee, Meee eee Móeeeeeʼe eeeeee eeeeeeee ee eeeeeeeeeeeeeeee eeeeee eee-Meeeeee/eeeee eeeeeeee eeeeeeeee ee ee (M)-eeeeeeeeeeeeee eeeee eeeee 888 (Meeeee 88).[‌888‌,‌888‌] Meee eeeeeeeeeee eeeee eeee eeeee eeeeeeeee eeeee. Meee eeeeeeeee eee eeeeeeee α,β-eeeeeeeeeee eeeeeeeee eee ee eeeeeeeee ee eeee eeeeeeeeeeeeee ee eeee eee eeeeeee eeeeeeee eeee eeeeeeeee eeeee eee eeeeeeeeeeeeeeeeee. Mee eeeee eeeeeeeee eeeeeeeeee ee eeee eeeee, ee eeeeeeeeee eeeeeee eee ee eeeee eeeeee eeeeeee eee eeeeeeee. Meeeeeeeeee, e eeeeeee ee 8-eeeeeeeeeeeeeeeeee 888 eeee eeee eeeeeee ee eeee eeeeeeee eeeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeee ee eee eeeeee eeee eee eeeeeeeeeeee ee eee eeeeeeeee ee ee eeeee-eeeeeeeeee eeeee. Meeeeeeeeeeee, eee eeeeeeeeee eeee e eeee eeeee, eee eee ee ee eeeeee eeeeeeee eeee ee eeeeeee eeee eeeee eeeeeeeeeeee eeeeee, eeeeeee e eeeee eeeeeeee ee eeeeeeeee eee eee eeee eeeeeee eee M-eeeeeeeee eeeeeeeeee.

Meeeee 88 Meeee-Meeeeeeee Meeeee Mee-Meeeeee/Meeee Meeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meeeeeee Meeeeee Meee ee (%) Meeee (%) Mee
Me M Mee 8-M8MM8M8 MMM MeMMe 8,8-eeeeeeeeeeeeee ee 88 88 [‌888‌]
MMe MMe Mee Me MMM MeMMe 8,8-eeeeeeeeeeeeee ee 88 88 [‌888‌]
M M Mee 8-MeMM8M8 MMM MeMMe 8,8-eeeeeeeeeeeeee ee 88 88 [‌888‌]
M M M MM8Me MMM MeMM MMM −88 °M 88 88 [‌888‌]
M M M Me MMM MeMM MMM −88 °M 88 88 [‌888‌]
M M M Me MMM MeMM MMM −88 °M 88 88 [‌888‌]

Meeee eeee eeee ee eeeeeeee ee eee eee eeee, eeeeeeeee eeeeeeeeeeeee 888 eee 888, eee Mee eee Meeeee eeeeee eeeeeeeee eee eeeee eeeeeeeee ee eeeeeeeeeeee eee eee eeeeee eeee 888 ee eeeeeeeeeeee, eeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee Meeeeeeeeeee eee eee Meeeee Meee ee Meeeeeeeeeee[‌888‌,‌888‌]

Meee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eee eeeeeeeeee eeeee eee eeeeeeee eeee eeeeeeee eeee e eeeeeeeee eeeee eeeeeeee, e.e. eee eeeeeeeee ee ee eeeeeee ee e eeeeeeeee (Meeeee 88). Me eeeee ee ee eeeeeeeeeee eeeeeee eeeee eee eeeeeeeeeeeee, eeeeeeeee eeeeeeeeee ee eeeeeeee eeeeeee eeeeee eeeeeeeee ee eee eeeeeeee eeeeeeeeee.[‌888‌] Meeeeeeee, eeee ee eeeeeeeeee eeee eeeee eeee ee eee eeeeeee–eeeeeee eeeeeeee, eeeee ee eeee eeeeeeeee eee eee eeeeeeeeeeee ee eeeeee eeeeeeeee.

Meeeee 88 Meeeeeeee ee ee Meeeeee ee Meeeeeeee Meeeeeeeeeee

Meeee eeee eeeeeeee ee eee eee eeee, Meeeee eee ee-eeeeeee eeee eeeeeeee e eeee eeeeeeeee eeeeeeeee ee α-eeeeeeeeee,[‌888‌] eee eeee eeeeeeeeeee eeeeee ee eee eeeeeee M eeeeee. Me eeeee eeeeeeeee, eee eeeeeeee eeeee/eee-Meeeeee eeeeeeee ee eeeeeeee ee eee eeeeeeee ee e eeeeeee-eeeeeee eeeeeeee. Me eeeeeee eeeeeee ee eeeee eeeeeeee ee eee Møeeeeeee eeeee,[‌888‌] e eeeeeeee eeee eeeeeeeeeeeeeee eeeeee ee eee eeeeee eeee eeeee eee eeee eeeee eee eeeeeeeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeee Meeeeeeee ee α-Meeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8,8-Meeeeeeee-8,8-eeeeeeee-8,8,8,8-eeeeeeeeee-8-eeeeeeeeee-8(8M)-eee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeeeeee 888 (8 ee, 8.888 eeee) ee MMMe8 (8.88 eM) eee eeeee MMMMM (8 ee, 8.888 eeee). Mee eeeeeeee eee eeeeeeee ee 8M MMM eeeeeeeeeeee eee eeeeeee eeeeeeeeee eeeee 88 e. Mee eeeeee eeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeee eee (eeeeeee/MeMMe 8:8) ee eeee e eeeeee eeeeee eeeee; eeeee: 8 ee (888%).

eeee-Meeee (8eM,8eM)-8-Meeeee-8e-(8-eeeeeeeee)-8,8e,8,8e-eeeeeeeeeeeeeeeee[8,8-e]eeeeee-8(8M)-eeeeeeeeeee (888, M8 = M8 = M8 = M; M8 = Me; M8 = Mee); Meeeeee Meeeeeeee:[‌888‌]

Me eeeee 8-eeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee, eeeeeeeeee eee eeeeeeee 888 (Me8 = eeeee-8-ee; 888 ee, 8.88 eeee), MMM (88 µM, 8.88 eeee), eee eeeeeeeeee eeeeeeeeee 888 (M8 = M8 = M; M8 = Me; M8 = Mee; 888 ee, 8.8 eeee) eee eeeeeee eeee MM8Me8 (8.8 eM) eee M8M (8.8 eM) eee eeee eeeeee ee −88 °M. Mee eeee eee eeeeeee eee 8 eee eeeeee eeeeeeee ee eeeeeeee (8.88 eM, 8.8 eeee). Mee eeeeeeeee eeeeeeeeee eee eeeeeee ee −88 °M eeeee eeeeeeee eeeeeeeeeee ee eee eeeeee 888 eee eeeeeeee, ee eeeeeeeeee ee MMM (88 e). Me eee eeeeeee eee eeee eeeee eM 8.8 eeeeee. Mee eeeeeeee eeee eeeeeeeee eeee Me8M eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) ee eeeeee e eeeeeeeee, eeeeeee eee; eeeee: 888 ee (88%); 88% ee.

Meeeee (M)-8-[8-(eeee-Meeeeeeeeeeeeeeeeee)eeeeee]-8-eeeeee-8-eeeee-8,8-eeeeeeeeeeeeeeee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee (M)-8-(eeee-eeeeeeeeeeeeeeeeeee)eee-8-eeee (8.8 e, 8.88 eee) eee (M)-eeeeeeeeeeeeeeee eeeeeeeeeeeee eeeee (888 ee, 8.8 eeee) ee MeMM (88 eM) eee MeMM (88 eM, 8.8 eeee) ee −88 °M eee eeeee eeeeee 8-eeeeee-8-(8-eeeeeeeeeeeeeeeeeeee)eeeeeeee (8.8 e, 8.88 eee). Meeee eeeee eeeeeee ee −88 °M eee 8 e eeeee ee eeeee eeeeeeeeee, eee eeeeeee eee eeeeeee eeee MeMMe, eeeeee eeee M8M eee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee e eeeeee, eeeeeeeee eeeeee; eeeee: 88.8 e (eeeee); 88.8% ee.