Regio- and diastereoselectivity in TiCl4-promoted reduction of 2-aryl-substituted cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes

被引：13

作者：

Morelli, CF

Fornili, A

Sironi, M

Duri, L

Speranza, G

Manittoa, P

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] Univ Milan, Dipartimento Chim Fis & Elettrochim, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(02)00687-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

TiCl4-mediated reduction of both syn- and anti-(4S,5S)-2-aryl-4-methyl-5-trifluoromethyl-1,3-dioxolanes with Et3SiD furnished monodeuterated hydroxy ethers resulting from the same regio- and stereoselective C-O bond cleavage (yields >80%; 82-92% de). Deuteride addition to the benzylidene acetal and removal of the alkyl moiety from the reaction product gave (R)-(alpha-H-2)benzy] alcohol (90% ee), thus suggesting a new route to chiral 1-deuteriobenzyl alcohols. A mechanistic rationale is proposed and supported by theoretical calculations. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：2609 / 2618

页数：10

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