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

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

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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",

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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

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