TiCl4-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base

Guigen Li; Han Xun Wei; Joe J. Gao; Thomas D. Caputo

doi:10.1016/S0040-4039(99)01992-9

TiCl₄-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base

Guigen Li, Han Xun Wei, Joe J. Gao, Thomas D. Caputo

Chemistry and Biochemistry

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

149 Scopus citations

Abstract

TiCl₄-Mediated Baylis-Hillman and aldol reactions were developed without the direct use of a Lewis base. These processes involve the conjugate addition of TiCl₄ to α,β-unsaturated substrates followed by carbonyl coupling. Baylis-Hillman olefins were obtained when α,β-unsaturated ketones were employed as the substrates, whereas β-halogenated aldol products were generated with an α,β-unsaturated N-acyl benzoxalinone as the Michael-type acceptor.

Original language	English
Pages (from-to)	1-5
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	1
DOIs	https://doi.org/10.1016/S0040-4039(99)01992-9
State	Published - Jan 1 2000

Keywords

Aldol reaction
Baylis-Hillman reaction
Titanium(IV) chloride

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10.1016/S0040-4039(99)01992-9

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title = "TiCl4-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base",

abstract = "TiCl4-Mediated Baylis-Hillman and aldol reactions were developed without the direct use of a Lewis base. These processes involve the conjugate addition of TiCl4 to α,β-unsaturated substrates followed by carbonyl coupling. Baylis-Hillman olefins were obtained when α,β-unsaturated ketones were employed as the substrates, whereas β-halogenated aldol products were generated with an α,β-unsaturated N-acyl benzoxalinone as the Michael-type acceptor.",

keywords = "Aldol reaction, Baylis-Hillman reaction, Titanium(IV) chloride",

author = "Guigen Li and Wei, {Han Xun} and Gao, {Joe J.} and Caputo, {Thomas D.}",

note = "Funding Information: We would like to dedicate this paper to Professor Richard A. Bartsch on the occasion of his 60th birthday. We gratefully acknowledge generous support from the Robert A. Welch Foundation (grant no. D-1361) and the South Plains Foundation. We also would like to thank Ms. Sun Hee Kim for her assistance.",

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T1 - TiCl4-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base

AU - Li, Guigen

AU - Wei, Han Xun

AU - Gao, Joe J.

AU - Caputo, Thomas D.

N1 - Funding Information: We would like to dedicate this paper to Professor Richard A. Bartsch on the occasion of his 60th birthday. We gratefully acknowledge generous support from the Robert A. Welch Foundation (grant no. D-1361) and the South Plains Foundation. We also would like to thank Ms. Sun Hee Kim for her assistance.

PY - 2000/1/1

Y1 - 2000/1/1

N2 - TiCl4-Mediated Baylis-Hillman and aldol reactions were developed without the direct use of a Lewis base. These processes involve the conjugate addition of TiCl4 to α,β-unsaturated substrates followed by carbonyl coupling. Baylis-Hillman olefins were obtained when α,β-unsaturated ketones were employed as the substrates, whereas β-halogenated aldol products were generated with an α,β-unsaturated N-acyl benzoxalinone as the Michael-type acceptor.

AB - TiCl4-Mediated Baylis-Hillman and aldol reactions were developed without the direct use of a Lewis base. These processes involve the conjugate addition of TiCl4 to α,β-unsaturated substrates followed by carbonyl coupling. Baylis-Hillman olefins were obtained when α,β-unsaturated ketones were employed as the substrates, whereas β-halogenated aldol products were generated with an α,β-unsaturated N-acyl benzoxalinone as the Michael-type acceptor.

KW - Aldol reaction

KW - Baylis-Hillman reaction

KW - Titanium(IV) chloride

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U2 - 10.1016/S0040-4039(99)01992-9

DO - 10.1016/S0040-4039(99)01992-9

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

TiCl₄-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base

Abstract

Keywords

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