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Goldfuss, B., Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014) 1, 375.
Deng and co-workers have investigated a series of chiral phase-transfer catalysts for the regioselective, asymmetric conjugate addition of cyanide to enones and α,β-unsaturated 1-acylpyrroles to give products 54 and 55. The best results are achieved using acetone cyanohydrin as the cyanide source and cupreidinium salt 52 or cupreinium salt 53, which provide products with S- and R-configurations, respectively (Scheme 51).[89]
Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee Meeeeeeee Meeee Meeee-Meeeeeee Meeeeeeee[88]
M8 | M8 | Meeeeeee | Meee (e) | Meeeee | ee (%) | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|
Me | Me | 88 (8 eee%) | 88 | M | 88 | 88 | [88] |
Me | Me | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | Me | 88 (8 eee%) | 88 | M | 88 | 88 | [88] |
Me | Me | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | (MM8)8Me | 88 (8 eee%) | 88 | M | 88 | 88 | [88] |
Me | (MM8)8Me | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | eMe | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | eMe | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | eMe | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | eMe | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | MM8MMMM | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
Me | MM8MMMM | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
8-Mee | Me | 88 (8 eee%) | 88 | M | 88 | 88 | [88] |
8-Mee | Me | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
8-MeMM8M8 | Me | 88 (8 eee%) | 88 | M | 88 | 88 | [88] |
8-MeMM8M8 | Me | 88 (88 eee%) | 88 | M | 88 | 88 | [88] |
8-MeM8M8 | Me | 88 (8 eee%) | 8 | M | 88 | 88 | [88] |
8-MeM8M8 | Me | 88 (88 eee%) | 8 | M | 88 | 88 | [88] |
M8 | Meeeeeee | Meee (e) | Meeeee | ee (%) | Meeee (%) | Mee |
---|---|---|---|---|---|---|
Me | 88 | 88 | M | 88 | 88 | [88] |
Me | 88 | 88 | M | 88 | 88 | [88] |
Me | 88 | 88 | M | 88 | 88 | [88] |
Me | 88 | 88 | M | 88 | 88 | [88] |
(MM8)8Me | 88 | 88 | M | 88 | 88 | [88] |
(MM8)8Me | 88 | 88 | M | 88 | 88 | [88] |
eMe | 88 | 88 | M | 88 | 88 | [88] |
eMe | 88 | 88 | M | 88 | 88 | [88] |
eMe | 88 | 88 | M | 88 | 88 | [88] |
eMe | 88 | 88 | M | 88 | 88 | [88] |
(MM8)8Me | 88 | 88 | M | 88 | 88 | [88] |
(MM8)8Me | 88 | 88 | M | 88 | 88 | [88] |
Meeeeeeee, Meeeeee eee ee-eeeeeee eeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeee eee eee eeeeeeeeeeeeeeee eeeeeeeee eeeeeeeee ee β-eeeeeeeeeeeee eeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeee Meeeeeeee ee β-Meee β-Meeeeeeeeeeeeee Meeeee[88]
Me8 | Me8 | ee (%) | Meeee (%) | Mee |
---|---|---|---|---|
Me | Me | 88 | 88 | [88] |
8-Mee | Me | 88 | 88 | [88] |
8-Mee | Me | 88 | 88 | [88] |
8-MeMM8M8 | Me | 88 | 88 | [88] |
8-MeM8M8 | Me | 88 | 88 | [88] |
8-MeM8M8 | Me | 88 | 88 | [88] |
8-eeeeeeee | Me | 88 | 88 | [88] |
Me | 8-Mee | 88 | 88 | [88] |
Me | 8-MeMM8M8 | 88 | 88 | [88] |
Me | 8-MeM8M8 | 88 | 88 | [88] |
Me | 8-MeM8M8 | 88 | 88 | [88] |
Me | 8-MeM8M8 | 88 | 88 | [88] |
Me | 8-M8MM8M8 | 88 | 88 | [88] |
Me | 8-eeeeeeee | 88 | 88 | [88] |
8,8-Me8M8M8 | 8-Me-8-MeM8M8 | 88 | 88 | [88] |
8,8-Me8M8M8 | 8-Mee | 88 | 88 | [88] |
Me ee eeeeeeeeeee eeeeeeee, Meeeeeeee eee ee-eeeeeee eeee eeeeeeee ee eeeeeeeeeeeee eeeeee eeeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeee ee e eeeeee ee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee (Meeeee 88).[88] Meeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee, eee eeeeee eeeeeeeee eee ee eeeeeee eeee eee eeeeeeee 88. Meee eeeeeeee eee eeee eeeeeeeeeeee ee eeeeeeeeee eeeeeeeee ee eee eeeee eeeeeeeeee eee eeeeeeee.[88]
Meeeee 88 Meeeeeeeeeeeeeeeee Meeeeeeee Meeeeeeee Meeee e Meeeee Meeeeeeee[88]
M8 | M8 | Meee (e) | eee | Meeeee (%) | Mee |
---|---|---|---|---|---|
Me | M | 8.8 | 88:88 | 88 | [88] |
Me | M | 8.88 | 88:88 | 88 | [88] |
eMe | M | 8.8 | 88:88 | 88 | [88] |
eMe | M | 8 | 88:88 | 88 | [88] |
Me | M | 8.88 | 88:88 | 88 | [88] |
8-MeM8M8 | M | 88.8 | 88:88 | 88 | [88] |
(MM8)8MMMMMM | M | 88 | 888:8 | 88e | [88] |
Me | Me | 88 | 88:88 | 88e | [88] |
e Meeeeeeee eeee eee eeeeeeee eeeeee ee eee eeeeeeeee eeeeeeeeeeeee.
e Meeeeeee eeeee ee eee eeeeeeee eeeeeeeeeeeee.
e M 88% eeeee ee eeeeeeee eeeeeeee eee eeee eeeeeeeee.
e M 88% eeeee ee eeeeeeee eeeeeeee eee eeee eeeeeeeee.
Meeeeeeeeeee Meeeeeeee
β-Meeee Meeeeee 88; Meeeeee Meeeeeeee:[88]
Mee eeeee (8.8 eeee), Me8MM8 (8.88 eeee), eee eeeeeeee 88 (8.888 eeee) ee 88 (8.88 eeee) eeee eeeeeeeee ee eeeeeee/MMMe8 (8:8; 8 eM) ee e 8-eeee eeee eeee e eeee-eeeee eeeeeee eee. Meee, eeeeeee eeeeeeeeeee (8.8 eeee) eee eeeee eee eee eeeeeee eee eeeeeee eeeeeeeeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeee eeee eee. ee MeMe (8 eM) eee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeee eeeeee eeee eeeeeeee, eeeee (Me8MM8), eee eeeeeeee eee eee eeeeeee eee eeee eeeeeee. Mee eeeeeee eee eeeeeeee eeeee eeeee eeeeeeeeeeeeee (eeeeee eee).
References
[89] | Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Mee, M.; Meeeee, M. M.; Meee, M., Meeee. Meee. Mee. Me., (8888) 88, 88888. |
[90] | Meeee, M.; Meeee, M.; Meeeeeee, M.; Meee, M.; Meeee, M.; Meeeeee, M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[91] | Meeeeeeee, M.; Meeeeee, M. M.; Meeeee, M. M., Meeeeee, (8888), 8888. |