Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes

John J. Masters; Louis S. Hegedus; Joaquín Tamariz

doi:10.1021/jo00019a038

Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes

John J. Masters, Louis S. Hegedus, Joaquín Tamariz

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

21 Scopus citations

Abstract

Alkylation of benzyl vinyl carbamate and propene with the anions of diethyl methylmalonate or dimethyl malonate in the presence of palladium(II) chloride, followed by cross-coupling or carbonylative cross-coupling with organostannanes, effected an overall dialkylation or alkylation/acylation of the monoolefin substrate. Complete control of stereochemistry in this palladium(II)-assisted reaction was observed using optically active ene carbamates affording β-amino-unsaturated keto esters in good chemical yields and excellent optical purity.

Original language	English
Pages (from-to)	5666-5671
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	56
Issue number	19
DOIs	https://doi.org/10.1021/jo00019a038
State	Published - 1 Sep 1991
Externally published	Yes

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title = "Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes",

abstract = "Alkylation of benzyl vinyl carbamate and propene with the anions of diethyl methylmalonate or dimethyl malonate in the presence of palladium(II) chloride, followed by cross-coupling or carbonylative cross-coupling with organostannanes, effected an overall dialkylation or alkylation/acylation of the monoolefin substrate. Complete control of stereochemistry in this palladium(II)-assisted reaction was observed using optically active ene carbamates affording β-amino-unsaturated keto esters in good chemical yields and excellent optical purity.",

author = "Masters, {John J.} and Hegedus, {Louis S.} and Joaqu{\'i}n Tamariz",

year = "1991",

month = sep,

day = "1",

doi = "10.1021/jo00019a038",

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volume = "56",

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journal = "Journal of Organic Chemistry",

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Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes. / Masters, John J.; Hegedus, Louis S.; Tamariz, Joaquín.
In: Journal of Organic Chemistry, Vol. 56, No. 19, 01.09.1991, p. 5666-5671.

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

TY - JOUR

T1 - Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes

AU - Masters, John J.

AU - Hegedus, Louis S.

AU - Tamariz, Joaquín

PY - 1991/9/1

Y1 - 1991/9/1

N2 - Alkylation of benzyl vinyl carbamate and propene with the anions of diethyl methylmalonate or dimethyl malonate in the presence of palladium(II) chloride, followed by cross-coupling or carbonylative cross-coupling with organostannanes, effected an overall dialkylation or alkylation/acylation of the monoolefin substrate. Complete control of stereochemistry in this palladium(II)-assisted reaction was observed using optically active ene carbamates affording β-amino-unsaturated keto esters in good chemical yields and excellent optical purity.

AB - Alkylation of benzyl vinyl carbamate and propene with the anions of diethyl methylmalonate or dimethyl malonate in the presence of palladium(II) chloride, followed by cross-coupling or carbonylative cross-coupling with organostannanes, effected an overall dialkylation or alkylation/acylation of the monoolefin substrate. Complete control of stereochemistry in this palladium(II)-assisted reaction was observed using optically active ene carbamates affording β-amino-unsaturated keto esters in good chemical yields and excellent optical purity.

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U2 - 10.1021/jo00019a038

DO - 10.1021/jo00019a038

M3 - Artículo

SN - 0022-3263

VL - 56

SP - 5666

EP - 5671

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Palladium(II)-Assisted Dialkylation and Alkylation/Acylation of Optically Active Ene Carbamates via Trialkylorganostannane Cross-Coupling and Carbonylative Coupling Processes

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