Unravelling the stereoselectivity in 6-exo-trig radical cyclization of α,β-unsaturated ester-tethered sugars. A tale of two stereocenters

被引：0

作者：

de Oliveira, Marcelo T. ^{[1
,2
]}

Cesar, Amary ^{[1
]}

Leal, Daniel H. S. ^{[2
]}

Prado, Maria A. F. ^{[2
]}

da Silva, Thais H. A. ^{[2
]}

Alves, Ricardo J. ^{[2
]}

机构：

[1] Univ Fed Minas Gerais, Inst Ciencias Exatas, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil

[2] Univ Fed Minas Gerais, Fac Farm, Dept Prod Farmaceut, BR-31270901 Belo Horizonte, MG, Brazil

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 07期

关键词：

DIELS-ALDER REACTIONS; THERMODYNAMIC CONTROL; ROTATIONAL-ISOMERISM; ORGANIC-SYNTHESIS; CHAIN REACTIONS; RING-CLOSURE; METHYL; REGIOSELECTIVITY; DENSITY; DESIGN;

D O I：

10.1039/b923414d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A computational investigation on the origin of the stereoselectivity of 6-exo-trig radical cyclization of alpha,beta-unsaturated ester-tethered sugars has revealed that a boat-like transition state, which keeps the ester in a planar conformation, holds the chiral information. Following this model, the stereocenter to which the ester functionality is connected reports the chirality to the newly formed stereocenter via a 1,4-transfer mechanism.

引用

页码：1619 / 1622

页数：4

共 13 条

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TETRAHEDRON LETTERS, 2002, 43 (42) : 7605 - 7608
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JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 10294 - 10298
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (31) : 6193 - 6195
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