Efficient Synthesis of Enantioenriched Isoxazoles by Chirality Transfer in Gold-Catalyzed Cyclization/Methylene-Group Transfer Followed by Carbonyl Ene Reaction

被引：12
|
作者：
Gima, Shinya [1 ]
Nakamura, Itaru [2 ]
Terada, Masahiro [1 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, 6-3 Aramaki Aza Aoba, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, 6-3 Aramaki Aza Aoba, Sendai, Miyagi 9808578, Japan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 30期
基金：
日本学术振兴会;
关键词：
Gold; Chirality; Ene reaction; Heterocycles; Synthetic methods; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC ALKYNYLATION; ORGANIC-SYNTHESIS; CHEMISTRY; ALDEHYDES; ALLENES; MEMORY;
D O I：
10.1002/ejoc.201700708
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioenriched isoxazoles having a chiral side chain at the 4-position were efficiently synthesized by chirality transfer in a gold-catalyzed cyclization/intermolecular methylene-transfer sequence followed by a carbonyl ene reaction. The chiral information of the enantioenriched O-propargylic oximes was completely retained during the gold-catalyzed reaction. The subsequent carbonyl ene reaction between the resulting 4-methylenated isoxazoline and glyoxylates proceeded with excellent levels of chirality transfer by using BF3OEt2 as a Lewis acid. According to the relationship of absolute configuration between the starting propargylic oxime and the obtained alcohol having an isoxazole, the carbonyl ene reaction proceeded in an endo manner.
引用
收藏
页码：4375 / 4378
页数：4
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