A novel reagent for the synthesis of geminal di-sulfones

Michael J. Hadd, Mark A. Smith, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A novel reagent (diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical α,β unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents.

Original languageEnglish (US)
Pages (from-to)5137-5140
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number31
DOIs
StatePublished - Jul 30 2001
Externally publishedYes

Fingerprint

Sulfones
Gems
Organophosphonates
Alkenes
Aldehydes
Stoichiometry
Isomers
Esters
phosphonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A novel reagent for the synthesis of geminal di-sulfones. / Hadd, Michael J.; Smith, Mark A.; Gervay-Hague, Jacquelyn.

In: Tetrahedron Letters, Vol. 42, No. 31, 30.07.2001, p. 5137-5140.

Research output: Contribution to journalArticle

Hadd, Michael J. ; Smith, Mark A. ; Gervay-Hague, Jacquelyn. / A novel reagent for the synthesis of geminal di-sulfones. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 31. pp. 5137-5140.
@article{a997b822fc1f4d488ef9ed8fed0bae63,
title = "A novel reagent for the synthesis of geminal di-sulfones",
abstract = "A novel reagent (diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical α,β unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents.",
author = "Hadd, {Michael J.} and Smith, {Mark A.} and Jacquelyn Gervay-Hague",
year = "2001",
month = "7",
day = "30",
doi = "10.1016/S0040-4039(01)01004-8",
language = "English (US)",
volume = "42",
pages = "5137--5140",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "31",

}

TY - JOUR

T1 - A novel reagent for the synthesis of geminal di-sulfones

AU - Hadd, Michael J.

AU - Smith, Mark A.

AU - Gervay-Hague, Jacquelyn

PY - 2001/7/30

Y1 - 2001/7/30

N2 - A novel reagent (diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical α,β unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents.

AB - A novel reagent (diisopropoxyphosphorylmethanesulfonylmethanesulfonylmethyl)-phosphonic acid diisopropyl ester (8) capable of forming symmetrical and non-symmetrical α,β unsaturated gem-disulfones is reported. Both aromatic and aliphatic aldehydes react in good yields to give exclusively the trans isomer. Selectivity for the mono-olefin can be achieved by varying the stoichiometry of reagents.

UR - http://www.scopus.com/inward/record.url?scp=0035974385&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035974385&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)01004-8

DO - 10.1016/S0040-4039(01)01004-8

M3 - Article

AN - SCOPUS:0035974385

VL - 42

SP - 5137

EP - 5140

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 31

ER -