Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

Duncan Gill; Nicholas H. Taylor; Eric J. Thomas

doi:10.1016/j.tet.2011.03.113

Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

Duncan Gill, Nicholas H. Taylor, Eric J. Thomas

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

15 Citations (Scopus)

Abstract

The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.

Original language	English
Pages (from-to)	5034-5045
Number of pages	12
Journal	Tetrahedron
Volume	67
Issue number	27-28
Early online date	16 Apr 2011
DOIs	https://doi.org/10.1016/j.tet.2011.03.113
Publication status	Published - 8 Jul 2011
Externally published	Yes

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title = "Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition",

abstract = "The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.",

keywords = "4-Methylenetetrahydropyran, Allyl silane, Ene reactions, oxy-Michael addition, Vinyl silane",

author = "Duncan Gill and Taylor, {Nicholas H.} and Thomas, {Eric J.}",

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doi = "10.1016/j.tet.2011.03.113",

language = "English",

volume = "67",

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T1 - Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

AU - Gill, Duncan

AU - Taylor, Nicholas H.

AU - Thomas, Eric J.

PY - 2011/7/8

Y1 - 2011/7/8

N2 - The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.

AB - The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.

KW - 4-Methylenetetrahydropyran

KW - Allyl silane

KW - Ene reactions

KW - oxy-Michael addition

KW - Vinyl silane

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U2 - 10.1016/j.tet.2011.03.113

DO - 10.1016/j.tet.2011.03.113

M3 - Article

AN - SCOPUS:79958723404

SN - 0040-4020

VL - 67

SP - 5034

EP - 5045

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -

Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

Abstract

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