Silylene transfer to α-keto esters and application to the synthesis of γ-lactones

Brett E. Howard, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

Disubstituted α-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to α-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The α-hydroxy acid products can be converted into γ-lactones using a variety of lactonization conditions.

Original languageEnglish (US)
Pages (from-to)6447-6453
Number of pages7
JournalTetrahedron
Volume65
Issue number33
DOIs
StatePublished - Aug 15 2009

Fingerprint

Hydroxy Acids
Lactones
Esters
Metals

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Silylene transfer to α-keto esters and application to the synthesis of γ-lactones. / Howard, Brett E.; Woerpel, Keith.

In: Tetrahedron, Vol. 65, No. 33, 15.08.2009, p. 6447-6453.

Research output: Contribution to journalArticle

@article{58352c89d5814dbf8c0c0b7b4a1e149e,
title = "Silylene transfer to α-keto esters and application to the synthesis of γ-lactones",
abstract = "Disubstituted α-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to α-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The α-hydroxy acid products can be converted into γ-lactones using a variety of lactonization conditions.",
author = "Howard, {Brett E.} and Keith Woerpel",
year = "2009",
month = "8",
day = "15",
doi = "10.1016/j.tet.2009.05.066",
language = "English (US)",
volume = "65",
pages = "6447--6453",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "33",

}

TY - JOUR

T1 - Silylene transfer to α-keto esters and application to the synthesis of γ-lactones

AU - Howard, Brett E.

AU - Woerpel, Keith

PY - 2009/8/15

Y1 - 2009/8/15

N2 - Disubstituted α-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to α-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The α-hydroxy acid products can be converted into γ-lactones using a variety of lactonization conditions.

AB - Disubstituted α-hydroxy acids have been synthesized by metal-catalyzed silylene transfer to α-keto esters. A range of substituents are tolerated in the transformation with the exception of branched groups at the vinylic position. The α-hydroxy acid products can be converted into γ-lactones using a variety of lactonization conditions.

UR - http://www.scopus.com/inward/record.url?scp=67650269821&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67650269821&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.05.066

DO - 10.1016/j.tet.2009.05.066

M3 - Article

AN - SCOPUS:67650269821

VL - 65

SP - 6447

EP - 6453

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 33

ER -