Stereospecific construction of chiral quaternary α-oxygenated aldehydes from chiral secondary alcohol derivatives

被引：12

作者：

Arasaki, H ^{[1
]}

Iwata, M ^{[1
]}

Nishimura, D ^{[1
]}

Itoh, A ^{[1
]}

Masaki, Y ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5025858, Japan

来源：

SYNLETT | 2004年 / 03期

关键词：

alpha; alpha-disubstituted alpha-oxyaldehyde; chiral synthesis; alpha-achloroepoxide; ring opening; methoxide anion;

D O I：

10.1055/s-2004-815406

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral tertiary dichloromethylcarbinol derivatives 2, prepared from protected chiral secondary alcohols 1, were converted stereospecifically into chiral quaternary alpha-oxygenated aldehyde derivatives 4 and 11 via intermediary alpha-chloroepoxides 3 under weakly basic conditions (K2CO3/MeOH/r.t.). The fashion generating the quaternary centers was proved to be quite different depending on the substrates: inversion of configuration of non-benzylic substrate 2a and apparent retention with benzylic one 2b.

引用

页码：546 / 548

页数：3

共 26 条

[1] A NEW PREPARATIVE ROUTE TO CHIRAL 2,3-EPOXY-1,4-BUTANEDIOLS [J].