Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1-fluoro-allo-inositol.

被引：12

作者：

Oppong, KA ^{[1
]}

Hudlicky, T ^{[1
]}

Yan, FY ^{[1
]}

York, CT ^{[1
]}

Nguyen, BV ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 10期

基金：

美国国家科学基金会;

关键词：

biooxidation; enantioselectivity; fluoroamino inositols; toluene dioxygenase;

D O I：

10.1016/S0040-4020(99)00080-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2875 / 2880

页数：6

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