Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

Masahiro Kawada; Kosuke Nakashima; Shin ichi Hirashima; Toru Sakagami; Yuji Koseki; Tsuyoshi Miura

doi:10.1002/chir.23015

Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

Masahiro Kawada, Kosuke Nakashima, Shin ichi Hirashima, Toru Sakagami, Yuji Koseki, Tsuyoshi Miura

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

1 Citation (Scopus)

Abstract

In this study, stereoselective conjugate addition of ketones to alkylidene malonates using organocatalyst has been developed. The reaction in the presence of 20 mol% of a novel thiourea-sulfonamide organocatalyst afforded conjugate adducts in moderate to high yields (up to 81%) under mild reaction conditions. Excellent diastereoselectivity (up to 98:2 dr) and enantioselectivity (up to 88% ee) were achieved.

Original language	English
Pages (from-to)	1215-1224
Number of pages	10
Journal	Chirality
Volume	30
Issue number	11
DOIs	https://doi.org/10.1002/chir.23015
Publication status	Published - 2018 Nov
Externally published	Yes

Keywords

alkylidene malonate
asymmetric conjugate addition
organocatalysis
organocatalyst
thiourea-sulfonamideIntroduction

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.23015

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title = "Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst",

abstract = "In this study, stereoselective conjugate addition of ketones to alkylidene malonates using organocatalyst has been developed. The reaction in the presence of 20 mol% of a novel thiourea-sulfonamide organocatalyst afforded conjugate adducts in moderate to high yields (up to 81%) under mild reaction conditions. Excellent diastereoselectivity (up to 98:2 dr) and enantioselectivity (up to 88% ee) were achieved.",

keywords = "alkylidene malonate, asymmetric conjugate addition, organocatalysis, organocatalyst, thiourea-sulfonamideIntroduction",

author = "Masahiro Kawada and Kosuke Nakashima and Hirashima, {Shin ichi} and Toru Sakagami and Yuji Koseki and Tsuyoshi Miura",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number 16K08178. The authors would like to thank Enago (WWW.ENAGO.JP) for the English language review. Publisher Copyright: {\textcopyright} 2018 Wiley Periodicals, Inc.",

year = "2018",

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doi = "10.1002/chir.23015",

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volume = "30",

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journal = "Chirality",

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T1 - Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

AU - Kawada, Masahiro

AU - Nakashima, Kosuke

AU - Hirashima, Shin ichi

AU - Sakagami, Toru

AU - Koseki, Yuji

AU - Miura, Tsuyoshi

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number 16K08178. The authors would like to thank Enago (WWW.ENAGO.JP) for the English language review. Publisher Copyright: © 2018 Wiley Periodicals, Inc.

PY - 2018/11

Y1 - 2018/11

N2 - In this study, stereoselective conjugate addition of ketones to alkylidene malonates using organocatalyst has been developed. The reaction in the presence of 20 mol% of a novel thiourea-sulfonamide organocatalyst afforded conjugate adducts in moderate to high yields (up to 81%) under mild reaction conditions. Excellent diastereoselectivity (up to 98:2 dr) and enantioselectivity (up to 88% ee) were achieved.

AB - In this study, stereoselective conjugate addition of ketones to alkylidene malonates using organocatalyst has been developed. The reaction in the presence of 20 mol% of a novel thiourea-sulfonamide organocatalyst afforded conjugate adducts in moderate to high yields (up to 81%) under mild reaction conditions. Excellent diastereoselectivity (up to 98:2 dr) and enantioselectivity (up to 88% ee) were achieved.

KW - alkylidene malonate

KW - asymmetric conjugate addition

KW - organocatalysis

KW - organocatalyst

KW - thiourea-sulfonamideIntroduction

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Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

Abstract

Keywords

ASJC Scopus subject areas

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