有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
二環性アミノアルコールを用いる不斉合成
田中 和彦
著者情報
ジャーナル フリー

1993 年 51 巻 7 号 p. 620-630

詳細
抄録

A wide variety of bicyclic amino alcohols have been prepared from D-camphor and screened as chiral elements in asymmetric synthesis. Endo-3-amino-endo-2-hydroxybornane and exo-3-amino-exo-2-hydroxybornane were found to be efficient chiral auxiliaries for the synthesis of optically pure cyclopropane derivatives, and [P]- and [M]-[7] heterohelicenes. Both (S)- and (R)-secondary alcohols are obtained with predictable stereochemistry by utilizing these diastereomeric amino alcohols as catalysts in the addition of diethylzinc to aldehydes and in reduction of aromatic ketones by borane. The shortest asymmetric synthesis of (R)-(-)-muscone with essentially 100% enantiomeric excess (ee) was accomplished by employing (1R, 2R, 3S, 4S)-3-[(1-methyl-2-pyrrolyl)methylamino]-1, 7, 7-trimethylbicylo[2.2.1]heptan-2-ol as a non-transferable ligand in the conjugate addition of alkoxydimethylcuprate to (E)-2-cyclopentadecenone. This asymmetric conjugate addition was promoted by use of 0.36 equivalents of the amino alcohol as a chiral catalyst, giving (R)-muscone in 99% ee and 86% chemical yield.

著者関連情報
© 社団法人 有機合成化学協会
前の記事 次の記事
feedback
Top