One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

Rory Devlin; David J. Jones; Gerard P. Mcglacken

doi:10.1021/acs.orglett.0c01874

One-Pot, Tandem Wittig Hydrogenation: Formal C(sp³)-C(sp³) Bond Formation with Extensive Scope

School of Chemistry

University College Cork

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

Abstract

A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.

Original language	English
Pages (from-to)	5223-5228
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.0c01874
Publication status	Published - 2 Jul 2020

Access to Document

10.1021/acs.orglett.0c01874

Cite this

@article{968b61f2b07e4eecb723ee7bc23bfa25,

title = "One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope",

abstract = "A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.",

author = "Rory Devlin and Jones, \{David J.\} and Mcglacken, \{Gerard P.\}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jul,

day = "2",

doi = "10.1021/acs.orglett.0c01874",

language = "English",

volume = "22",

pages = "5223--5228",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - One-Pot, Tandem Wittig Hydrogenation

T2 - Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

AU - Devlin, Rory

AU - Jones, David J.

AU - Mcglacken, Gerard P.

PY - 2020/7/2

Y1 - 2020/7/2

N2 - A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.

AB - A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.

UR - https://www.scopus.com/pages/publications/85087528411

U2 - 10.1021/acs.orglett.0c01874

DO - 10.1021/acs.orglett.0c01874

M3 - Article

C2 - 32574057

AN - SCOPUS:85087528411

SN - 1523-7060

VL - 22

SP - 5223

EP - 5228

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

One-Pot, Tandem Wittig Hydrogenation: Formal C(sp³)-C(sp³) Bond Formation with Extensive Scope

Abstract

Access to Document

Other files and links

Fingerprint

Cite this