Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

J F  Bower; C J  Martin; D J  Rawson; A M Z  Slawin; J M J  Williams

Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

J F Bower, C J Martin, D J Rawson, A M Z Slawin, J M J Williams

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

44 Citations (Scopus)

Abstract

The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96:4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97: 3 selectivity in the absence of any additional chiral agents.

Original language	English
Pages (from-to)	333-342
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	4
Publication status	Published - 21 Feb 1996

Keywords

DIELS-ALDER REACTIONS
OXIDATION
DERIVATIVES
DIENOPHILES
ACID

Cite this

@article{771ab47353a847ec949842d3634aa9ed,

title = "Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction",

abstract = "The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96:4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97: 3 selectivity in the absence of any additional chiral agents.",

keywords = "DIELS-ALDER REACTIONS, OXIDATION, DERIVATIVES, DIENOPHILES, ACID",

author = "Bower, {J F} and Martin, {C J} and Rawson, {D J} and Slawin, {A M Z} and Williams, {J M J}",

year = "1996",

month = feb,

day = "21",

language = "English",

pages = "333--342",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "4",

}

TY - JOUR

T1 - Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

AU - Bower, J F

AU - Martin, C J

AU - Rawson, D J

AU - Slawin, A M Z

AU - Williams, J M J

PY - 1996/2/21

Y1 - 1996/2/21

N2 - The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96:4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97: 3 selectivity in the absence of any additional chiral agents.

AB - The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96:4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97: 3 selectivity in the absence of any additional chiral agents.

KW - DIELS-ALDER REACTIONS

KW - OXIDATION

KW - DERIVATIVES

KW - DIENOPHILES

KW - ACID

M3 - Article

SN - 0300-922X

SP - 333

EP - 342

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 4

ER -

Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

Abstract

Keywords

Fingerprint

Cite this