Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols

James M. Takacs; Xun Tian Jiang; Alexei P. Leonov

doi:10.1016/S1268-7731(03)00074-2

Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols

James M. Takacs
, Xun Tian Jiang
, Alexei P. Leonov

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

15 Scopus citations

Abstract

The triethylborane-promoted and palladium-catalyzed reactions of 2, 4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)₂ with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)₂ and Ph ₃P affords in the catalyzed reactions of dienyl acetates.

Original language	English
Pages (from-to)	7075-7079
Number of pages	5
Journal	Tetrahedron Letters
Volume	44
Issue number	37
DOIs	https://doi.org/10.1016/S1268-7731(03)00074-2
State	Published - Sep 8 2003

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title = "Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols",

abstract = "The triethylborane-promoted and palladium-catalyzed reactions of 2, 4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)2 with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)2 and Ph 3P affords in the catalyzed reactions of dienyl acetates.",

author = "Takacs, \{James M.\} and Jiang, \{Xun Tian\} and Leonov, \{Alexei P.\}",

note = "Funding Information: Support from the NIH under grant GM34927 is gratefully acknowledged. The NMR spectrometers used for these studies were purchased with shared instrument grant funds (NIH SIG-1-510-RR-06307) and (NSF CHE-0091975).",

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doi = "10.1016/S1268-7731(03)00074-2",

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T1 - Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols

AU - Takacs, James M.

AU - Jiang, Xun Tian

AU - Leonov, Alexei P.

N1 - Funding Information: Support from the NIH under grant GM34927 is gratefully acknowledged. The NMR spectrometers used for these studies were purchased with shared instrument grant funds (NIH SIG-1-510-RR-06307) and (NSF CHE-0091975).

PY - 2003/9/8

Y1 - 2003/9/8

N2 - The triethylborane-promoted and palladium-catalyzed reactions of 2, 4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)2 with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)2 and Ph 3P affords in the catalyzed reactions of dienyl acetates.

AB - The triethylborane-promoted and palladium-catalyzed reactions of 2, 4-dienyl alcohols or the corresponding isomeric divinyl alcohols with bis(trifluoroethyl) malonates provide an improved method for the regio- and stereoselective dienylation of malonates. The phosphine ligand is an important control element in the reaction. Combinations of Pd(OAc)2 with BIPHEP or BINAP give dienylated malonates in good yield and higher isomeric purity than the traditional combination of Pd(OAc)2 and Ph 3P affords in the catalyzed reactions of dienyl acetates.

UR - https://www.scopus.com/pages/publications/0043160106

U2 - 10.1016/S1268-7731(03)00074-2

DO - 10.1016/S1268-7731(03)00074-2

M3 - Article

AN - SCOPUS:0043160106

SN - 0040-4039

VL - 44

SP - 7075

EP - 7079

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Palladium-catalyzed regiocontrolled and stereoselective alkylations of bis(trifluoroethyl) malonates with dienyl alcohols

Abstract

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