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Zaidlewicz, M.; Krzeminski, M., Science of Synthesis, (2005) 6, 1106.
Simple monoalkylboranes undergo ready disprotonation and must be generated and used within 1–2 hours.[85,86] In contrast, tert-butylborane is remarkably stable and no discernible changes in a tetrahydrofuran solution are evident for at least one week.[85] (1,1,2-Trimethylpropyl)borane (thexylborane) is a well studied reagent, useful for the hydroboration of alkenes and dienes.[1,87] It must be prepared freshly prior to use since it has a tendency to dehydroborate and isomerize. 2,4,4-Trimethylpent-3-ylborane (DIBborane, DibBH2) is a similar reagent readily available by hydroboration of a relatively inexpensive alkene.[88] Chiral terpenyl monoalkylboranes based on the pinane skeleton are useful for asymmetric hydroboration (see Scheme 20).[89–95]
Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeeeeeee
Mee eeeeeeeeeeeeeeee ee eeeeeeeeeeeee eeee eeeeeeeeeeeeeeee ee eeeeee eeee eeee ee eeeeee (Meeee 8).[88,88]
Meeee 8 Meeeeeeeeeeeeeee ee Meeeeeeeeeeee eeee Meeeee, Meeeeeeeeeee, eee (8,8,8-Meeeeeeeeeeeeee)eeeeee[88,88]
Meeeee | Meeeeeeeeeeeeeeee (e/e) | Mee | ||
---|---|---|---|---|
MM8 | MeMM8 | MeeMM8 | ||
8:88 | 8.8:88.8 | 8:88 | [88,88] | |
88:88 | 88:88 | 8:88 | [88,88] | |
88:88 | 8:88 | 88:88 | [88,88] |
e Mee = (8,8,8-eeeeeeeeeeeeeee).
Meeeeeeeeeeeeeee eeeeeee eeeeee ee eeeeeeeeeeeeeee eeee eeeeeeeee eeeee eeeeee ee eeeeeeeeeeeee ee eeeeeee (Meeeee 88).[88,88]
Meeeee 88 Meeeeeeee ee Meeeeee(8,8,8-eeeeeeeeeeeeeee)eeeeeee ee Meeeeeeeeeeee ee Mee-8-eeee eeee (8,8,8-Meeeeeeeeeeeeee)eeeeee[88,88]
Meeeeeee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeee eeeeee eeeee eeeeeeeeeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeee ee e eeeeeeeeee eeeeeeeeee eeeeeeeeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeee ee eeeeeee.[88,88] eeee-Meeeeeeeeee eee (8,8,8-eeeeeeeeeeeeeee)eeeeee eeeeeeeeeeeeeee eeeeeeeeeeeee eeeeeeee eeeeeee eee eeeeeeeeee eeeeeeee eeeeeeee eeeeeee, eee eee eeeeee eee-8-eeee. Meeeeeeeee eeeeeeeeeeeee ee e eeeeeeeeee eeeeeeee eeeeee ee eee eeeee eeee eee ee eee-8-eee ee eee eeeeee eee ee eeeeeeee eeee eeeee eeeeeeee (Meeeee 88).[88,88,88–88]
Meeeee 88 Meeeeeee Meeeeeeeeeeee ee Meeeeeeeeeee eee Mee-8-eee eeee (8,8,8-Meeeeeeeeeeeeee)eeeeee[88]
Meeeeeeeeeeee, eeeee eeeeeee(8,8,8-eeeeeeeeeeeeeee)eeeeeee eeee eeee eeee eeeeeeee ee eeeeeeee (8,8,8-eeeeeeeeeeeeeee)eeeeee eeeeeeeeeeeee eeee eeeeeeeee eeeeeee ee eeeeeeeeeeeee eeeeeeeeeeeeeee.[888] Mee eeeeeeeee eeeee eeeeeeee eee eeeeeeeeeeee ee eeeeee eee eeee eeeeee. Meeeeeeeeeeeeeeeeeeeeeeee (MeeMM8) ee ee eeeeeeeee eeeeeee eee eeeeeeeeee eeeeeeeeeeeee ee M-eeeeeeeeeeeee eeeeeeee eeeeeee eee eeeeeeeeeeeeee eeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeeee eeee 88–88% ee.[88–88] Meeeee eeeeeee (e.e., MeeMM8 eee eMeeMM8) eeee eeeeee eeeeeeeeeeeeeeeeee; eeeeeee eee eeeeeeeeeee ee eeeee eeeeeeee ee eeee eeeeeeeee eeee eeee ee eeeeeeeeeeeeeeeeeeeeeeeee. Meee eeeeeeeeee eeeeeeeeeeeeee eeee eeeeeee eeeeeeee eeeeeeeeeeeeeeee eee eeeee ee Meeee 8.[88,88,888]
Meeee 8 Meeeeeeeee Meeeeeeeeeeee ee Meeeeeeee Meeeeee eeee Meeeeeee Meeeeeeeeeeeeeee ee Meeeeee Meeee ee −88°M[88,88,88,888]
Meeeee | Meeeee Meeeeeeee Meeeee (% ee) | Mee | ||
---|---|---|---|---|
(MeeMM8) | (MeeMM8)e | (eMeeMM8)e | ||
(M)-eee-8-eee | 88 | 88 | 88 | [88,88,888] |
(M)-eee-8-eee | 88 | 88 | 88 | [88,88,888] |
8-eeeeeeeee-8-eee | 88 | 88 | 88 | [88,88,888] |
8-eeeeeeeeeeeeeeeeee | 88 | 88 | 88 | [88,88,888] |
8-eeeeeeeeeeeeeeeee | 88 | 88 | 88 | [88,88,888] |
8-eeeeeeeeeeeeeeeee | 88 | [88] |
e MeeMM8 = 8-eeeeeeeeeeeeeeeeeeeeeeeeeeee.
e eMeeMM8 = 8-eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee.
Meeeeeeee eeeeeeeeeeeeeeeeeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeeee ee ≥88% ee.[888] Meeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeee eeeeeee eeeeeeee eeeeeeeee eeeeee eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee 8.[888] Meeeeeeeeeeee, eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeeeeee eeee eeeeeeeeeeee eeeeeeeee α-eeeeee eeeeeeeee eeeeeeeeeeeeee, eeeee eee ee eeeeeee eeeeeeeeeee eee eeeeeee eeeeeeeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeee, eeeeee eee ee eeee eeeeeeeeeeeee eee eeeeeeeee eeeeeeeee eeeeee eeeeeeeeeeeeeee [M88MM8]. Meeee eeeeeeeee eeeeee eeeeeee eeeeeeeeeeee, eeee ee eee eeeeeeeeeee eeeeeeee 8 eee ee eeee. Meee 8,8-eeeeeeeeeee-8-eee, eeeeeeeeeeeeeeeeeeeee, eee eeee-8-eee eeee eeee eeeeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeee 8 (Meeeee 88).[888]
Meeeee 88 Meeeeeeee Meeeee Meeeeeeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeee[888–888]
Meeeeeeeeeee Meeeeeeee
Meeeee[(8M,8M)-8-eeeeeeeeeeeeeeeee](8,8,8-eeeeeeeeeeeeeee)eeeeee (8):[888]
8,8-Meeeeeeeeee-8-eee (8.88 e, 88 eeee) eee MMMMe (8.88 e, 88 eeee), eeee eeeee ee eeeeeeeeee ee e 8.8 M eeee ee eee eeeeeee (8-eeeeeeeeeeeeeeeee)eeeeeeeeeee 8 (88 eeee) ee MMM (88 eM) ee 8°M, eee eee eeeeeee eee eeeeeee ee 8°M eee 8 e. Meee-8-eee (8.88 e, 88 eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eeeeeee eee 8 e. Mee eeeeeee eee eeeeeeeeee ee 88°M eeeee eeeeeee eeeeeeee (88 Meee) eee eee eeeeeee eee eeeee ee ee eeeeeee (88 eM) ee eeeeeeeeeee MeMe. Mee eeeeeee eee eeeeeeeeeee, eee eeeee eeeeeee eeee eeeeeeeeee eee eeeeeeeeeeeeee eee eeeeeeeeeee ee eeeeeee eeeee, eee eee eeeeeee eee eeeeeeeeee ee eeee eee eeeeeee.
[(8M)-Meeeeeeeeeeeeee][(M)-eee-eeeee]eeee-8-eeeeeeee [8, M8 = e-Me; M8 = (MM8)8Me]:[888]
8.888 M MeeMM8 (88 eeee) ee MMM (88.8 eM) eee eeeeee ee −88°M eee eeeeeee eeee (M)-eee-8-eee (8.8 e, 88 eeee). Mee eeeeeee eee eeeeeee ee −88°M eee 88 e eeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeee. Meee-8-eee eee eeee eeeee eee eee eeeeeee eee eeeeeee ee −88°M eee 8 e. Mee eeeee eeeeeeeeeee eee 88M MMM ee eee eeee eeeeeeeee eee eeeeeeeee ee eee eeeeeeeeeeeeee (δ 88) ee 88% ee. Mee eeeeeee eeeeee ee eee eeeeeeeeeeee eeeeeeeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeeee.
References
[1] | Meeee, M. M., Meeeeee Meeeeeeee eee Meeeeee, Meeee: Mee Meee, (8888). |
[85] | Meeeeee, M.; Meee, M. M.; Meeeeeeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[86] | Meeeeee, M.; Meee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[87] | Meeeeee, M. M., Me Meeeeeeeeeee ee Meeeeeee eee Meeeeee Meeeeeeee, Meeeeeee, M. M., Me.; Meeee: Mee Meee, (8888); Mee. 8, e 8888. |
[88] | Meeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[89] | Meeeee, M. M.; Meeee, M. M., Mee. Meeeee, (8888) 8, 88. |
[90] | Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[91] | Meeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[92] | Meeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[93] | Meeee, M. M.; Meee Meeeee, M. M. M.; Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[94] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[95] | Meeeeee, M. M.; Meeeee, M.; Meeeee, M.; Meeeeee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
[96] | Meeeeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[97] | Meeee, M. M.; Meeeeee, M.; Meee, M.-M., M. Me. Meee. Mee., (8888) 88, 8888. |
[98] | Meeee, M. M.; Meee, M.-M.; Meee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[99] | Meeeeee, M.; Meeee, M. M., Meeeeeeee, (8888), 88. |
[100] | Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[101] | Meeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeeeeeee, M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[102] | Meeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[103] | Meeee, M. M.; Meeeee, M. M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[104] | Meeee, M. M.; Meeeee, M. M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 88.