Studies on the diastereoselective reductive alkylation of (R)-phenylglycinol derived phthalimide:: observation of stereoelectronic effects

被引:47
作者
Chen, MD [1 ]
He, MZ [1 ]
Zhou, X [1 ]
Huang, LQ [1 ]
Ruan, YP [1 ]
Huang, PQ [1 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Key Lab Chem Biol Fujian Province, Xiamen 361005, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
isoindolin-1-one; phenylglycinol; reductive alkylation; diastereoselective reaction; stereoelectronic effects;
D O I
10.1016/j.tet.2004.10.109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Full details of a flexible approach to N-protected (R)-3-alkyl-isoindolin-1-ones 13 via diastereoselective reductive-alkylation are described, with emphasis on the stereochemical outcome of the key diastereoselective reactions. Additional experiments allowed finding remarkable stereoelectronic effects on the reductive ring-opening reactions. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1335 / 1344
页数:10
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