Diastereoselective synthesis of enantiopure 5-[2-(alkoxyalkyl)-1-(hydroperoxypropyl)]-3-alkoxycarbonyl-2-alkyl furans

被引：12

作者：

Lattanzi, A ^{[1
]}

Sagulo, F ^{[1
]}

Scettri, A ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, Salerno, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(99)00187-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diastereoselective approach to enantiomerically pure furyl hydroperoxides of general type 1 has been accomplished starting from (S)-(-)-ethyl lactate. In the first part of the synthesis the alkylating reagents 7a,b were efficiently produced to be used in the second part for a 4-step known methodology to obtain furyl hydroperoxides. The most relevant transformation of the synthesis is the first reported diastereoselective iodoenoletherification of 2-acetyl-4-heptenoate esters 8a,b possessing a phi-chiral center. Furthermore, the final radical oxidation performed on (E)-5-alkylidene-4,5-dihydrofurans 11a,b led to formation of hydroperoxides (S,S)-12a,b in a diastereocontrolled manner due to 1,2-asymmetric induction. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2023 / 2035

页数：13

共 64 条

[1] Horseradish peroxidase-catalyzed enantioselective reduction of racemic hydroperoxy homoallylic alcohols:: A novel enzymatic method for the preparation of optically active, unsaturated diols and hydroperoxy alcohols [J].