A new preparation of homochiral N-protected 5-hydroxy-3-piperidenes, promising chiral building blocks, by palladium-catalyzed deracemization of their alkyl carbonates

被引：12
作者：
Takahata, Hiroki [1 ]
Suto, Yurniko [1 ]
Kato, Erina [1 ]
Yoshimura, Yuichi [1 ]
Ouchi, Hidekazu [1 ]
机构：
[1] Tohoku Univ, Fac Pharmaceut Sci, Sendai, Miyagi 9818558, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 4-5期
关键词：
chiral building blocks; deracemization; N-protected alkyl carbonates of 5-hydroxy-3-piperidenes; N-protected; 5-hydroxy-3-piperidenes;
D O I：
10.1002/adsc.200600559
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The palladium-catalyzed deracemization of N-protected alkyl carbonates of 5-hydroxy-3-piperidenes by use of chiral phosphine ligands is described. A Trost ligand such as (R)-BPA was found to be a suitable chiral ligand for the deracemization, providing N-protected 5-hydroxy-3-piperidenes in good yields with good to high enantioselectivities. A plausible mechanism for the reaction is proposed.
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收藏
页码：685 / 693
页数：9
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