Synthesis and odor of optically active rose oxide

被引：50

作者：

Yamamoto, T ^{[1
]}

Matsuda, H ^{[1
]}

Utsumi, Y ^{[1
]}

Hagiwara, T ^{[1
]}

Kanisawa, T ^{[1
]}

机构：

[1] Takasago Int Corp, Cent Res Lab, Hiratsuka, Kanagawa 2540073, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 50期

关键词：

diastereomer; rose oxide; odor; cyclization; (3R)- and (3S)-citronellol; (3R)- and (3S)-3,7-dimethyl-5,6-octadien-1-ol; Pd-(R)- and (S)-BINAP complexes;

D O I：

10.1016/S0040-4039(02)02311-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereo selective synthesis of optically active rose oxide (1) by KHSO4 and Pd-BINAP-catalyzed cyclization of (3R)- and (3S)-3,7-dimethyl-6,7-octadien-1-ol (5) is described. One-pot synthesis of the (3R)- and (3S)-allenyl alcohol 5 from (3R)- and (3S)-citronellol (2) (98% ee) is also described. Furthermore, the odor properties of the four diastereomers of 1 are reported. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：9077 / 9080

页数：4

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