Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones

Jian Wang; Hao Li; Liansuo Zu; Wei Wang

doi:10.1002/adsc.200505420

Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones

Jian Wang
, Hao Li
, Liansuo Zu
, Wei Wang

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

91 Scopus citations

Abstract

A highly enantioselective, organocatalytic Michael addition reaction of unmodified ketones with chalcones has been developed for the first time. The process, catalyzed by (S)-N-(pyrrolidin-2-ylmethyl)-trifluoromethanesulfonamide, affords 1,5-diketones in high yields (73-89%) and with high degrees of enantio- and diastereoselectivity (86-97% ee, > 30:1 dr).

Original language	English (US)
Pages (from-to)	425-428
Number of pages	4
Journal	Advanced Synthesis and Catalysis
Volume	348
Issue number	4-5
DOIs	https://doi.org/10.1002/adsc.200505420
State	Published - Mar 2006
Externally published	Yes

Keywords

Asymmetric catalysis
Enones
Ketones
Michael addition
Organic catalysis
Pyrrolidine-sulfonamides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200505420

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title = "Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones",

abstract = "A highly enantioselective, organocatalytic Michael addition reaction of unmodified ketones with chalcones has been developed for the first time. The process, catalyzed by (S)-N-(pyrrolidin-2-ylmethyl)-trifluoromethanesulfonamide, affords 1,5-diketones in high yields (73-89\%) and with high degrees of enantio- and diastereoselectivity (86-97\% ee, > 30:1 dr).",

keywords = "Asymmetric catalysis, Enones, Ketones, Michael addition, Organic catalysis, Pyrrolidine-sulfonamides",

author = "Jian Wang and Hao Li and Liansuo Zu and Wei Wang",

year = "2006",

month = mar,

doi = "10.1002/adsc.200505420",

language = "English (US)",

volume = "348",

pages = "425--428",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "4-5",

}

TY - JOUR

T1 - Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones

AU - Wang, Jian

AU - Li, Hao

AU - Zu, Liansuo

AU - Wang, Wei

PY - 2006/3

Y1 - 2006/3

N2 - A highly enantioselective, organocatalytic Michael addition reaction of unmodified ketones with chalcones has been developed for the first time. The process, catalyzed by (S)-N-(pyrrolidin-2-ylmethyl)-trifluoromethanesulfonamide, affords 1,5-diketones in high yields (73-89%) and with high degrees of enantio- and diastereoselectivity (86-97% ee, > 30:1 dr).

AB - A highly enantioselective, organocatalytic Michael addition reaction of unmodified ketones with chalcones has been developed for the first time. The process, catalyzed by (S)-N-(pyrrolidin-2-ylmethyl)-trifluoromethanesulfonamide, affords 1,5-diketones in high yields (73-89%) and with high degrees of enantio- and diastereoselectivity (86-97% ee, > 30:1 dr).

KW - Asymmetric catalysis

KW - Enones

KW - Ketones

KW - Michael addition

KW - Organic catalysis

KW - Pyrrolidine-sulfonamides

UR - https://www.scopus.com/pages/publications/33645929387

UR - https://www.scopus.com/pages/publications/33645929387#tab=citedBy

U2 - 10.1002/adsc.200505420

DO - 10.1002/adsc.200505420

M3 - Article

AN - SCOPUS:33645929387

SN - 1615-4150

VL - 348

SP - 425

EP - 428

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 4-5

ER -

Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones

Abstract

Keywords

ASJC Scopus subject areas

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