Highly stereoselective synthesis of trisubstituted cyclohexanols using a guanidine-catalyzed tandem Henry-Michael reaction

Qipu Dai; Huicai Huang; John Cong-Gui Zhao

doi:10.1021/jo4001806

Highly stereoselective synthesis of trisubstituted cyclohexanols using a guanidine-catalyzed tandem Henry-Michael reaction

Qipu Dai, Huicai Huang, John Cong-Gui Zhao^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

A highly diastereoselective (dr >99:1) and enantioselective (ee value up to 98%) synthesis of trisubstituted cyclohexanols was achieved by using a tandem Henry - Michael reaction between nitromethane and 7-oxo-hept-5-enals catalyzed by the Misaki-Sugimura guanidine.

Original language	English
Pages (from-to)	4153-4157
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	78
Issue number	8
DOIs	https://doi.org/10.1021/jo4001806
Publication status	Published - 19 Apr 2013
Externally published	Yes

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title = "Highly stereoselective synthesis of trisubstituted cyclohexanols using a guanidine-catalyzed tandem Henry-Michael reaction",

abstract = "A highly diastereoselective (dr >99:1) and enantioselective (ee value up to 98%) synthesis of trisubstituted cyclohexanols was achieved by using a tandem Henry - Michael reaction between nitromethane and 7-oxo-hept-5-enals catalyzed by the Misaki-Sugimura guanidine.",

author = "Qipu Dai and Huicai Huang and {Cong-Gui Zhao}, John",

year = "2013",

month = apr,

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doi = "10.1021/jo4001806",

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journal = "Journal of Organic Chemistry",

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AU - Dai, Qipu

AU - Huang, Huicai

AU - Cong-Gui Zhao, John

PY - 2013/4/19

Y1 - 2013/4/19

N2 - A highly diastereoselective (dr >99:1) and enantioselective (ee value up to 98%) synthesis of trisubstituted cyclohexanols was achieved by using a tandem Henry - Michael reaction between nitromethane and 7-oxo-hept-5-enals catalyzed by the Misaki-Sugimura guanidine.

AB - A highly diastereoselective (dr >99:1) and enantioselective (ee value up to 98%) synthesis of trisubstituted cyclohexanols was achieved by using a tandem Henry - Michael reaction between nitromethane and 7-oxo-hept-5-enals catalyzed by the Misaki-Sugimura guanidine.

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U2 - 10.1021/jo4001806

DO - 10.1021/jo4001806

M3 - Article

AN - SCOPUS:84876591560

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SP - 4153

EP - 4157

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Highly stereoselective synthesis of trisubstituted cyclohexanols using a guanidine-catalyzed tandem Henry-Michael reaction

Abstract

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