Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products

Yen Ku Wu; Rongrong Lin; F. G. West

doi:10.1055/s-0036-1588769

Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products

Yen Ku Wu, Rongrong Lin, F. G. West

Chemistry (Twin Cities)

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

4 Scopus citations

Abstract

A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.

Original language	English (US)
Article number	st-2017-r0080-l
Pages (from-to)	1486-1490
Number of pages	5
Journal	Synlett
Volume	28
Issue number	12
DOIs	https://doi.org/10.1055/s-0036-1588769
State	Published - Jul 24 2017

Keywords

Morita-Baylis-Hillman alkylation
allenol ethers
carbonyl umpolung
interrupted Nazarov cyclization
oxyallyl cation

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title = "Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products",

abstract = "A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.",

keywords = "Morita-Baylis-Hillman alkylation, allenol ethers, carbonyl umpolung, interrupted Nazarov cyclization, oxyallyl cation",

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AU - Lin, Rongrong

AU - West, F. G.

PY - 2017/7/24

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N2 - A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.

AB - A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita-Baylis-Hillman alkylation process.

KW - Morita-Baylis-Hillman alkylation

KW - allenol ethers

KW - carbonyl umpolung

KW - interrupted Nazarov cyclization

KW - oxyallyl cation

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Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products

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