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Forgione, P.; Fader, L. D., Science of Synthesis, (2008) 36, 565.
The reduction of epoxy alkynes (e.g., 110) is a useful method to generate chiral, tertiary propargylic alcohols and has been employed en route to the synthesis of acetylenic allenophanes (Scheme 56).[114]
Meeeee 88 M Meeeee Meeeeeee Meeeeeeeeee Meeeeee eee Meeeeee Meeeeeeee[888]
α-Meeeeee eeeeeeeee eee ee eeeeeeeee eeee eeeeeeeee eeeeeeeeeee eeeeeeee eeee ee 888 eee eee Meeee–Meeee eeeeeeeeeeeeee ee eeeeeeeee, e.e. 888, ee eeeeeeee eeeeeee, e.e. 888, eeeee eee ee eeeeeeeeeee ee eeeeeeee eee eeee eeeeeeeeeee eeeeeee. Meee eeeeee eee eeeeeeee ee eee eeeeeeeeeeeeeeee eeeee eeeeeeeee ee eeeeeeeeeeeee (Meeeee 88).[888]
Meeeee 88 M Meeeeeeeeee Meeeeee eee Meeee–Meeee Meeeeeee ee ee α-Meeeeee Meeeeeee[888]
Meeeee eeeeeeeeeee eeeeeeee eee ee eeeeeeee eee e eee-eeee eeeeeeee eeee eeeeeeee eee eeeeeeee ee ee α-eeeee eeeee, eeeeeee eeee eeeeeeeeeee eeeeeeeeee eeeeeeeeee 888, ee eeeeeeeee, eeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee 888, eee eeeeeeeeee eeeeeeeeeee ee eeeee eeeeee eeeeeeee eeeeeeeeeee eeeeeeee 888 ee eeeeeeeeeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeee 888, eeeeeeeee ee eee eeeeeeeeee eeeeee (Meeeee 88).[888] Meeeeeee eee eeeeeeeeeee ee eee eee eeeeeeeeeeeee eeeeeeee eee eeeeeee eeeeeeeeeee eeeeeeeee eeeeeee ee eeee eeeeeeeeeeeeeeeeee, eee eeeeeee eeeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeeeee eeeeeeeee 888 ee eee eeeeeeeee eeeeeeee eeee eee eeeeeeeeeee, eeeee eeeeeeee eeeeee eee eeeeeeeeeeeee ee eeee eeeeee. Mee eeeeeeeeeee eeeeeeee ee 888 eeeeeeeee eeeee eeee eeee eeeeee eeee M8 = 8-eeeee, eee eeee eeeeee eeee M8 = eeee-eeeee. Meeeeee, eee eeee-eeeee eeeeeeeee ee eeeeeeeee ee eeeeeee eee eeeeeeeeeeeeeeeeeeee ee eee eeeeeee eeeee eeeeeeee ee eee eeeeeeeee.
Meeeee 88 Meeeee Meeeeeeeeee Meeeeeee eee Meeeeeeeee Meeeeeeeee Meeee Meeeeeee–Meeeeeeeeee ee Meeeeeeee[888]
Mee eeeeee eeeeeeeeeee ee 8-(eeeeeeeeeeee)-8,8-eeeeeeeee eeeeeeeeeeeee 888 ee eeeeee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee 888, eeeee eee eeeeeeeee ee eee ee ee eeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeeee, eee ee eeeeee, eeeeeeeeeeee ee eee eeeeeeeee ee eeee-eeeee eeeeeeeeeee eeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeee Meeeeeeeeee Meeeeeee eee Meeeee Meeeeeeeeee ee e Meeeeeeee[888]
Meeeeeeee eeeeeeeeeee eeee eeee eeee eeeeeeee ee eeeeeee eeeeee eeeeeeeeeee eeeeeeee.[888,888]
Meeeeeeeeeee Meeeeeeee
(MM,M)- eee (MM,M)-(M)-8-Meeeee-8-(8-eeeeeeeeeeeee)-8-(eeeeeeeeeeeeee)eeee-8-ee-8-ee (888, M8 = 8-Mee; M8 = Me; M8 = Me); Meeeeee Meeeeeeee:[888]
Me e eeee ee eMe8MM (8.888 eM, 8.88 eeee) ee MMM (8.88 eM) eee eeeee 8.88 M MeMe ee eeeeeee (8.88 eM, 8.88 eeee) ee 8°M, eee eee eeeeeee eee eeeeeee eee 88 eee. Mee eeeeeee eee eeeeee ee −888°M, eee eeee e eeee ee eeeee eeeeeeeee 888 (M8 = 8-Mee; M8 = Me; 88.8 ee, 8.88 eeee) ee MMM (8.8 eM) eee eeeee eeeeeeee eeee 88 eee. Mee eeeeeee eee eeeeeee eee ee eeeeeeeeee 88 eee. MeMMM (8.888 eM, 8.88 eeee) eee eeee eeeee, eee eee eeeeeee eee eeeeeee eee 88 eee; eee eeee eee eeeeeeee eeee eee. ee MM8Me (8 eM) eeeee eeeeeeee eeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8, eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee. Meeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8) eeee (MM,M)-888; eeeee: 88 ee (88%) eee (MM,M)-888; eeeee: 88 ee (88%). (MM,M)-888: ee 888–888°M; [α]M88 +888.8 (e 8.88, MeMM); 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M), 8.88 (e, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, 8M), 8.88 (e, 8M). (MM,M)-888: ee 888–888°M; [α]M88 +888.8 (e 8.88, MeMM); 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M), 8.88 (e, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, 8M), 8.88 (e, 8M).
(M)-8-Meeeeeeeee-8-ee-8-ee (888M, M8 = Me); Meeeeee Meeeeeeee:[888]
Me e eeeeeeeeee ee MeM (88 ee, 8.88 eeee) ee MMM (8.8 eM) eee eeeee eeeeeeeee (M)-888 (M8 = 8-Mee, M8 = Me, M8 = Me; 888 ee, 8.88 eeee) ee MMM (8.8 eM) ee 8°M. Mee eeeeeee eee eeeeeee eee 88 eee, eee eeee eee eeeeeeee eeee eee. ee MM8Me (8 eM) eeeee eeeeeeee eeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8, eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8) ee eeee 888M; eeeee: 88 ee (88%); [α]M88 −88.8 (e 8.8, MMMe8); 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M), 8.88 (ee, M = 8.8, 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M); MM (eeee) ν̃eee:8888, 8888, 8888 ee−8. Meee eeeeeeeee eee e eeeeee eeeeeeeeeeeeeeee eeeeeeee eeeeeeee; eeeee: 8.8 ee (8%).
(M)-8-Meeeee-8-(eeeeeeeeeeeeee)eeee-8-ee-8-ee (888M, M8 = Me; M8 = Me); Meeeeee Meeeeeeee:[888]
M eeee ee eeeeeeeee (M)-888 (M8 = 8-Mee, M8 = Me, M8 = Me; 888 ee, 8.88 eeee) ee eeeeeee (8.8 eM) eee eeeeee eeeee eeeeee eee 8 e. Mee eeeeeee eee eeee eeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8) ee eeee eee eeeeeee; eeeee: 88 ee (88%); [α]M88 −88.8 (e 8.88, MMMe8); 8M MMM (MMMe8, δ): 8.88–8.88 (e, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, 8M).
References
[114] | Meeeee, M. M.; Meee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[115] | Meeeeee, M.; Meeee, M.; Meeee, M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 888. |
[116] | Meeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 888. |
[117] | Meee, M.; Meee, M.-M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[118] | Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 8888. |
[119] | Meeeeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee: Meeeeeeee, (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.