Asymmetric synthesis of (S,S)- and (R,R)-2-methylthreitol

被引：11

作者：

Enders, Dieter ^{[1
]}

Peiffer, Evelyn ^{[1
]}

Raabe, Gerhard ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

SYNTHESIS-STUTTGART | 2007年 / 07期

关键词：

asymmetric synthesis; epoxidation; tetrols; alpha-alkylation; SAMP/RAMP hydrazones; 1,2-addition;

D O I：

10.1055/s-2007-965967

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of (SS)- and (R,R)-2-methylthreitol was carried out, starting from the SAMP or RAMP hydrazone of 2,2-dimethyl-1,3-dioxan-5-one. The protocol involves an enantioselective alpha-alkylation as a key step. The second stereogenic center was installed by either nucleophilic 1,2-addition or diastereoselective epoxidation with bis(acetylacetonato)oxovanadium(IV) [VO(acac)(2)] as catalyst. The title compounds were obtained in excellent diastereo- and enantiomeric excesses (>= 98% de, 98% ee) and in good overall yields (40-61%).

引用

页码：1021 / 1026

页数：6

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