Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

高等学校化学研究 ›› 1999, Vol. 15 ›› Issue (1): 23-28.

Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

HUANG Jin-xia, LI Yan, MA Xing-quan, ZHOU Zhong-qiang

Department of Chemistry, Hubei University, Wuhan, 430062

收稿日期:1998-04-20 出版日期:1999-01-24 发布日期:2011-08-17
通讯作者: HUANG Jin-xia
基金资助:
Supported by the National Natural Science Foundation of China.

Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

HUANG Jin-xia, LI Yan, MA Xing-quan, ZHOU Zhong-qiang

Department of Chemistry, Hubei University, Wuhan, 430062

Received:1998-04-20 Online:1999-01-24 Published:2011-08-17
Supported by:
Supported by the National Natural Science Foundation of China.

摘要/Abstract

摘要： (+)-Camphor derived N-crotonoylsultam 2, readily available from chiral auxiliary bornane-10,2-sultam and crotonoyl chloride, reacted with selected Grignard reagent 3(R= n-butyl, n-pentyl, n-hexyl, n-heptyl) under the control of CuI or not being at low temperatures, giving diasteroisomers 4, 5 respectively. After nondestructive cleavage both enantiomers of the acid and alcohol were obtained in high e. e.%. The d. e.% of 4,5 was determined by HPLC, and the assignment of these values was discussed by analyzing ¹H NMR(500 MHz).

关键词: Bornanesultam, N-Crotonoly sultam, Michael addition, Synthesis

Abstract: (+)-Camphor derived N-crotonoylsultam 2, readily available from chiral auxiliary bornane-10,2-sultam and crotonoyl chloride, reacted with selected Grignard reagent 3(R= n-butyl, n-pentyl, n-hexyl, n-heptyl) under the control of CuI or not being at low temperatures, giving diasteroisomers 4, 5 respectively. After nondestructive cleavage both enantiomers of the acid and alcohol were obtained in high e. e.%. The d. e.% of 4,5 was determined by HPLC, and the assignment of these values was discussed by analyzing ¹H NMR(500 MHz).

Key words: Bornanesultam, N-Crotonoly sultam, Michael addition, Synthesis

HUANG Jin-xia, LI Yan, MA Xing-quan, ZHOU Zhong-qiang . Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam[J]. 高等学校化学研究, 1999, 15(1): 23-28.

HUANG Jin-xia, LI Yan, MA Xing-quan, ZHOU Zhong-qiang . Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam[J]. Chemical Research in Chinese Universities, 1999, 15(1): 23-28.

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Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

Synthesizing β-Chiral Carbon Alkanoic Acids and Alcohols via (-)-Bornane-10,2-crotonoylsultam

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