Multifunctional Asymmetric Catalysis
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概要
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Two types of general and practical enantioselective catalysts, namely, bimetallic complexes and Lewis acid-Lewis base bifunctional catalysts were developed based on the concept of multifunctional catalysis. In the first part of this review, the first example of a catalytic enatioselective nitro-Mannick reaction as well as a direct catalytic enantioselective aldol reaction of 2-hydroxyacetophenone using bimetallic complexes is discussed. The new complex, composed of ytterbium, potassium, and BINOL in a ratio of 1 : 1 : 3, promoted the nitro-Mannich reaction of nitromethane with up to 91% ee. On the other hand, second generation ALB catalyzed an enantioselective and diastereoselective nitro-Mannich reaction of nitroalkanes in up to 83% ee with a diastereomeric ratio up to 7 : 1. Moreover, the reaction of aldehydes with 2-hydroxyacetophenone in the presence of LLB, KHMDS, and H_2O selectively gave the corresponding anti-α, β-dihydroxy ketones in up to 95% ee and, in the presence of the catalyst prepared from linked-BINOL and 2 eq of Et_2Zn, selectively afforded the syn-α, βdihydroxy ketones in up to 86% ee. In the second part, the development of new catalysts displaying a Lewis acidity and a Lewis basicity is described. The Lewis acid of the catalyst activates aldehydes, imines, acyl quinoliniums, and ketones. At the same time, the Lewis base activates the nucleophile(TMSCN). Catalysts of this type produced a highly enantioselective cyanation of these electrophiles. Application of the catalytic enantioselective cyanosilylation of aldehydes to a total synthesis of epothilones is also described.
- 公益社団法人日本薬学会の論文
- 2001-05-01
著者
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柴崎 正勝
東大 大学院
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金井 みち子
Finnigan Mat Instruments Inc.
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KANAI Motomu
Graduate School of Pharmaceutical Sciences, The University of Tokyo
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SHIBASAKI Masakatsu
Graduate School of Pharmaceutical Sciences, The University of Tokyo
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金井 求
Graduate School Of Pharmaceutical Sciences The University Of Tokyo
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Kanai Motomu
Graduate School Of Pharmaceutical Science The University Of Tokyo
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Shibasaki Masakatsu
Graduate School Of Pharmaceutical Science The University Of Tokyo
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