An efficient entry to optically active anti- and syn-β-amino-α-trifluoromethyl alcohols

被引：29

作者：

Fustero, Santos ^{[1
,2
]}

Albert, Laia ^{[1
,2
]}

Acena, Jose Luis ^{[2
]}

Sanz-Cervera, Juan F. ^{[1
,2
]}

Asensio, Amparo ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

[2] Ctr Invest Principe Felipe, Lab Mol Organ, E-46013 Valencia, Spain

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 04期

关键词：

D O I：

10.1021/ol702947n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

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页码：605 / 608

页数：4

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