Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions

Qi Lai; Yang Li; Zhiyong Gong; Qingwen Liu; Chiyu Wei; Zhiguang Song

doi:10.1002/chir.22540

Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions

Qi Lai, Yang Li, Zhiyong Gong, Qingwen Liu, Chiyu Wei, Zhiguang Song^*

^*Corresponding author for this work

Jilin University

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

6 Citations (Scopus)

Abstract

Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L-thiazoline-thiourea derivatives were used. A plausible transition state model is proposed to explain the observed enantioselectivities. Chirality 27:979-988, 2015.

Original language	English
Pages (from-to)	979-988
Number of pages	10
Journal	Chirality
Volume	27
Issue number	12
DOIs	https://doi.org/10.1002/chir.22540
Publication status	Published - 1 Dec 2015
Externally published	Yes

Keywords

asymmetric Michael addition
chiral catalyst
thiazoline
thiourea

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10.1002/chir.22540

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abstract = "Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L-thiazoline-thiourea derivatives were used. A plausible transition state model is proposed to explain the observed enantioselectivities. Chirality 27:979-988, 2015.",

keywords = "asymmetric Michael addition, chiral catalyst, thiazoline, thiourea",

author = "Qi Lai and Yang Li and Zhiyong Gong and Qingwen Liu and Chiyu Wei and Zhiguang Song",

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T2 - Design and Application in Enantioselective Michael Reactions

AU - Lai, Qi

AU - Li, Yang

AU - Gong, Zhiyong

AU - Liu, Qingwen

AU - Wei, Chiyu

AU - Song, Zhiguang

PY - 2015/12/1

Y1 - 2015/12/1

N2 - Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L-thiazoline-thiourea derivatives were used. A plausible transition state model is proposed to explain the observed enantioselectivities. Chirality 27:979-988, 2015.

AB - Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitrostyrenes. The products with S configuration were obtained in 98% enantiomeric excess (ee) when the L-thiazoline-thiourea derivatives were used. A plausible transition state model is proposed to explain the observed enantioselectivities. Chirality 27:979-988, 2015.

KW - asymmetric Michael addition

KW - chiral catalyst

KW - thiazoline

KW - thiourea

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SN - 0899-0042

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SP - 979

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JO - Chirality

JF - Chirality

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ER -

Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions

Abstract

Keywords

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