Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides)

Guigen Li; Han Xun Wei; Jason D. Hook

doi:10.1016/S0040-4039(99)00756-X

Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides)

Guigen Li, Han Xun Wei, Jason D. Hook

Chemistry and Biochemistry

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

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Abstract

Ytterbium(III) triflate has been found to catalyze anionic additions of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides) in a cosolvent system (Et₂O- CH₂Cl₂). This new system has made it possible to utilize those p- toluenesulfinimines of low solubility in Et₂O as the electrophiles to react with anionic (α-carbalkoxyvinyl)cuprates for the asymmetric synthesis of the corresponding β-mono and β,β-disubstituted Baylis-Hillman adducts. Modest yields (51.0-64.4% yield) and good to excellent diastereoselectivities (>90% de) were obtained.

Original language	English
Pages (from-to)	4611-4614
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(99)00756-X
State	Published - Jun 18 1999

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title = "Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides)",

abstract = "Ytterbium(III) triflate has been found to catalyze anionic additions of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides) in a cosolvent system (Et2O- CH2Cl2). This new system has made it possible to utilize those p- toluenesulfinimines of low solubility in Et2O as the electrophiles to react with anionic (α-carbalkoxyvinyl)cuprates for the asymmetric synthesis of the corresponding β-mono and β,β-disubstituted Baylis-Hillman adducts. Modest yields (51.0-64.4% yield) and good to excellent diastereoselectivities (>90% de) were obtained.",

author = "Guigen Li and Wei, {Han Xun} and Hook, {Jason D.}",

note = "Funding Information: We gratefully acknowledget he Robert A. Welch Foundation (Grant No. D-1361) for supporting this work.",

year = "1999",

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doi = "10.1016/S0040-4039(99)00756-X",

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T1 - Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides)

AU - Li, Guigen

AU - Wei, Han Xun

AU - Hook, Jason D.

N1 - Funding Information: We gratefully acknowledget he Robert A. Welch Foundation (Grant No. D-1361) for supporting this work.

PY - 1999/6/18

Y1 - 1999/6/18

N2 - Ytterbium(III) triflate has been found to catalyze anionic additions of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides) in a cosolvent system (Et2O- CH2Cl2). This new system has made it possible to utilize those p- toluenesulfinimines of low solubility in Et2O as the electrophiles to react with anionic (α-carbalkoxyvinyl)cuprates for the asymmetric synthesis of the corresponding β-mono and β,β-disubstituted Baylis-Hillman adducts. Modest yields (51.0-64.4% yield) and good to excellent diastereoselectivities (>90% de) were obtained.

AB - Ytterbium(III) triflate has been found to catalyze anionic additions of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides) in a cosolvent system (Et2O- CH2Cl2). This new system has made it possible to utilize those p- toluenesulfinimines of low solubility in Et2O as the electrophiles to react with anionic (α-carbalkoxyvinyl)cuprates for the asymmetric synthesis of the corresponding β-mono and β,β-disubstituted Baylis-Hillman adducts. Modest yields (51.0-64.4% yield) and good to excellent diastereoselectivities (>90% de) were obtained.

UR - http://www.scopus.com/inward/record.url?scp=0033581029&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00756-X

DO - 10.1016/S0040-4039(99)00756-X

M3 - Article

AN - SCOPUS:0033581029

VL - 40

SP - 4611

EP - 4614

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 25

ER -

Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides)

Abstract

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