Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives

Caroline Marchi; Elisenda Trepat; Marcial Moreno-Mañas; Adelina Vallribera; Elies Molins

doi:10.1016/S0040-4020(02)00538-0

Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives

Caroline Marchi, Elisenda Trepat, Marcial Moreno-Mañas, Adelina Vallribera, Elies Molins

Department of Chemistry

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

21 Citations (Scopus)

Abstract

Relative syn 1,2-hydrazinoalcohols have been prepared through diastereoselective Ni(II)-catalyzed Michael addition of chiral derivatives of acetoacetic acid and of 3-oxostearic acid to dialkyl azodicarboxylates, followed by stereoselective reduction of the keto function. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	5699-5708
Journal	Tetrahedron
Volume	58
Issue number	28
DOIs	https://doi.org/10.1016/S0040-4020(02)00538-0
Publication status	Published - 8 Jul 2002

Keywords

Chiral induction
Conjugate addition
Kinetic resolution
Nickel catalysis
Syn-1,2-hydrazinoalcohol
β-ketoacid derivatives

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title = "Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives",

abstract = "Relative syn 1,2-hydrazinoalcohols have been prepared through diastereoselective Ni(II)-catalyzed Michael addition of chiral derivatives of acetoacetic acid and of 3-oxostearic acid to dialkyl azodicarboxylates, followed by stereoselective reduction of the keto function. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

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author = "Caroline Marchi and Elisenda Trepat and Marcial Moreno-Ma{\~n}as and Adelina Vallribera and Elies Molins",

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Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives. / Marchi, Caroline; Trepat, Elisenda; Moreno-Mañas, Marcial; Vallribera, Adelina; Molins, Elies.

In: Tetrahedron, Vol. 58, No. 28, 08.07.2002, p. 5699-5708.

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

TY - JOUR

T1 - Ni(II)-catalyzed Michael additions. Part 2: Dynamic kinetic resolution in the reduction of chiral α-hydrazino-β-ketoacid derivatives

AU - Marchi, Caroline

AU - Trepat, Elisenda

AU - Moreno-Mañas, Marcial

AU - Vallribera, Adelina

AU - Molins, Elies

PY - 2002/7/8

Y1 - 2002/7/8

N2 - Relative syn 1,2-hydrazinoalcohols have been prepared through diastereoselective Ni(II)-catalyzed Michael addition of chiral derivatives of acetoacetic acid and of 3-oxostearic acid to dialkyl azodicarboxylates, followed by stereoselective reduction of the keto function. © 2002 Elsevier Science Ltd. All rights reserved.

AB - Relative syn 1,2-hydrazinoalcohols have been prepared through diastereoselective Ni(II)-catalyzed Michael addition of chiral derivatives of acetoacetic acid and of 3-oxostearic acid to dialkyl azodicarboxylates, followed by stereoselective reduction of the keto function. © 2002 Elsevier Science Ltd. All rights reserved.

KW - Chiral induction

KW - Conjugate addition

KW - Kinetic resolution

KW - Nickel catalysis

KW - Syn-1,2-hydrazinoalcohol

KW - β-ketoacid derivatives

U2 - 10.1016/S0040-4020(02)00538-0

DO - 10.1016/S0040-4020(02)00538-0

M3 - Article

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SP - 5699

EP - 5708

JO - Tetrahedron

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SN - 0040-4020

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