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

Publisher link

10.1055/s-0036-1588769

Find It

Find It at U of M Libraries

Cite this

@article{fe4812abf8534ab4aed87f4c943bf0ac,

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",

author = "Wu, {Yen Ku} and Rongrong Lin and West, {F. G.}",

year = "2017",

month = jul,

day = "24",

doi = "10.1055/s-0036-1588769",

language = "English (US)",

volume = "28",

pages = "1486--1490",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "12",

}

TY - JOUR

T1 - Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl-vinyl Anion Equivalents to Access Formal Morita-Baylis-Hillman Alkylation Products

AU - Wu, Yen Ku

AU - Lin, Rongrong

AU - West, F. G.

PY - 2017/7/24

Y1 - 2017/7/24

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

UR - http://www.scopus.com/inward/record.url?scp=85017629588&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85017629588&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1588769

DO - 10.1055/s-0036-1588769

M3 - Article

AN - SCOPUS:85017629588

SN - 0936-5214

VL - 28

SP - 1486

EP - 1490

JO - Synlett

JF - Synlett

IS - 12

M1 - st-2017-r0080-l

ER -

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

Abstract

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this