A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water

Siang en Syu; Tzu Ting Kao; Wenwei Lin

doi:10.1016/j.tet.2009.11.093

A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water

Siang en Syu, Tzu Ting Kao, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

49 Citations (Scopus)

Abstract

(S)-2-((Naphthalen-2-ylsulfonyl)methyl)pyrrolidine, prepared in three steps from (S)-N-Boc-2-[((4-toluenesulfonyl)oxy)methyl]pyrrolidine in 62% overall yield, was used as a new type of organocatalyst bearing a pyrrolidine and a sulfone moiety. It shows very high catalytic activity toward the direct asymmetric Michael reaction of cyclohexanone and nitroolefins. All the corresponding adducts can be furnished in 90-99% yields and with up to 98% ee and over 99:1 dr on water in the presence of this catalyst (15 mol %) without any additive.

Original language	English
Pages (from-to)	891-897
Number of pages	7
Journal	Tetrahedron
Volume	66
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2009.11.093
Publication status	Published - 2010 Jan 23

Keywords

Ketones
Michael addition
Nitroolefins
Organocatalysis
Stereoselectivity

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.11.093

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title = "A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water",

abstract = "(S)-2-((Naphthalen-2-ylsulfonyl)methyl)pyrrolidine, prepared in three steps from (S)-N-Boc-2-[((4-toluenesulfonyl)oxy)methyl]pyrrolidine in 62% overall yield, was used as a new type of organocatalyst bearing a pyrrolidine and a sulfone moiety. It shows very high catalytic activity toward the direct asymmetric Michael reaction of cyclohexanone and nitroolefins. All the corresponding adducts can be furnished in 90-99% yields and with up to 98% ee and over 99:1 dr on water in the presence of this catalyst (15 mol %) without any additive.",

keywords = "Ketones, Michael addition, Nitroolefins, Organocatalysis, Stereoselectivity",

author = "Syu, {Siang en} and Kao, {Tzu Ting} and Wenwei Lin",

note = "Funding Information: We gratefully acknowledge the National Science Council of the Republic of China (NSC Grant No. 97-2113-M-003-003-MY2) and National Taiwan Normal University (97031008) for financial support. ",

year = "2010",

month = jan,

day = "23",

doi = "10.1016/j.tet.2009.11.093",

language = "English",

volume = "66",

pages = "891--897",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water

AU - Syu, Siang en

AU - Kao, Tzu Ting

AU - Lin, Wenwei

N1 - Funding Information: We gratefully acknowledge the National Science Council of the Republic of China (NSC Grant No. 97-2113-M-003-003-MY2) and National Taiwan Normal University (97031008) for financial support.

PY - 2010/1/23

Y1 - 2010/1/23

N2 - (S)-2-((Naphthalen-2-ylsulfonyl)methyl)pyrrolidine, prepared in three steps from (S)-N-Boc-2-[((4-toluenesulfonyl)oxy)methyl]pyrrolidine in 62% overall yield, was used as a new type of organocatalyst bearing a pyrrolidine and a sulfone moiety. It shows very high catalytic activity toward the direct asymmetric Michael reaction of cyclohexanone and nitroolefins. All the corresponding adducts can be furnished in 90-99% yields and with up to 98% ee and over 99:1 dr on water in the presence of this catalyst (15 mol %) without any additive.

AB - (S)-2-((Naphthalen-2-ylsulfonyl)methyl)pyrrolidine, prepared in three steps from (S)-N-Boc-2-[((4-toluenesulfonyl)oxy)methyl]pyrrolidine in 62% overall yield, was used as a new type of organocatalyst bearing a pyrrolidine and a sulfone moiety. It shows very high catalytic activity toward the direct asymmetric Michael reaction of cyclohexanone and nitroolefins. All the corresponding adducts can be furnished in 90-99% yields and with up to 98% ee and over 99:1 dr on water in the presence of this catalyst (15 mol %) without any additive.

KW - Ketones

KW - Michael addition

KW - Nitroolefins

KW - Organocatalysis

KW - Stereoselectivity

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U2 - 10.1016/j.tet.2009.11.093

DO - 10.1016/j.tet.2009.11.093

M3 - Article

AN - SCOPUS:72149122415

SN - 0040-4020

VL - 66

SP - 891

EP - 897

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

A new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water

Abstract

Keywords

ASJC Scopus subject areas

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