Benzyl and Phenylthiomethyl Silanes: A New Class of Bifunctional Linchpins for Type II Anion Relay Chemistry (ARC)

被引：28
作者：
Smith, Amos B., III [1 ]
Tong, Rongbiao [1 ]
机构：
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 06期
关键词：
COMPLEX NATURAL-PRODUCTS; FORMAL SYNTHESIS; CARBON BOND; CONSTRUCTION; STEREOCHEMISTRY; SILYLCARBINOL; SPONGISTATINS; REARRANGEMENT; RING;
D O I：
10.1021/ol100130x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new class of bifunctional linchpins bearing electrophilic sites beta or gamma to a silyl group have been designed, synthesized, and demonstrated to be competent In tricomponent unions exploiting Type II Anion Relay Chemistry (ARC). High diastereoselectivities were observed when a phenyl moiety (R-2) served as an anion-stabilizing group (ASG) adjacent to a methyl susbtituent (R-1), while diastereomeric mixtures were obtained when a phenylthiol moiety served as the ASG, irrespective of alpha-substitution.
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页码：1260 / 1263
页数：4
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