Asymmetric synthesis using chirally modified borohydrides. Part 3. Enantioselective reduction of ketones and oxime ethers with reagents prepared from borane and chiral amino alcohols
作者:Shinichi Itsuno、Michio Nakano、Koji Miyazaki、Hirofumi Masuda、Koichi Ito、Akira Hirao、Seiichi Nakahama
DOI:10.1039/p19850002039
日期:——
The asymmetric reduction of aromatic and aliphatic ketones, halogeno ketones, hydroxy ketones, keto esters, and ketone oxime ethers with reagents prepared from borane and chiral amino alcohols has been investigated. When α,α-diphenyl β-amino alcohols, such as (2S,3R)-(–)-2-amino-3-methyl-1,1 -diphenylpentanol (2d), were used as a chiral auxiliary, very high enantioselectivities (ca. 90 % e.e.) were
研究了由硼烷和手性氨基醇制得的试剂对芳香族和脂肪族酮,卤代酮,羟基酮,酮酯和酮肟醚的不对称还原。当使用(2 S,3 R)-(–)-2-氨基-3-甲基-1,1-二苯基戊醇(2d)等α,α-二苯基β-氨基醇作为手性助剂时在还原各种酮和肟醚时,具有很高的对映选择性(约90%ee)。