CONSTRUCTION OF ALL-CARBON QUATERNARY STEREOCENTERS BY ZINC-MEDIATED BARBIER-TYPE ALLYLATION IN AQUEOUS MEDIA

被引：9
|
作者：
Takao, Ken-ichi [1 ]
Miyashita, Tomo [1 ]
Akiyama, Nozomi [1 ]
Kurisu, Takuya [1 ]
Tsunoda, Kohei [1 ]
Tadano, Kin-ichi [1 ]
机构：
[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
来源：
HETEROCYCLES | 2012年 / 86卷 / 01期
关键词：
Quaternary Stereocenter; Barbier Reaction; Diastereoselective Reaction; Aqueous Medium; CATALYTIC ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC TOTAL-SYNTHESIS; ENT-HYPERFORIN; ALDEHYDES; ADDITIONS; REAGENTS; HALIDES; ACID;
D O I：
10.3987/COM-12-S(N)31
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective construction of an all-carbon quaternary stereocenter by Barbier-type allylation in aqueous media is described. Sugar-derived aldehydes, 2,3-O-isopropylidene-D-glyceraldehyde and 2,4-O-benzylidene-D-threose, were reacted with geranyl chloride in the presence of zinc powder to provide gamma-adducts bearing quaternary stereocenters with good stereoselectivity.
引用
收藏
页码：147 / 153
页数：7
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