(2S, 3S, 5S)- and (2S, 3S, 5R)-5-carboxaldehyde-2,3-diphenyl-1,4-dioxane as surrogates for optically pure 2,3-O-isopropylideneglyceraldehyde in asymmetric synthesis

Jeffrey Aubé, Craig J. Mossman, Susan Dickey

Research output: Research - peer-reviewArticle

  • 13 Citations

Abstract

The title compounds were prepared from threo-hydrobenzoin, either enantiomer of which is readily available from trans-stilbene using the Sharpless asymmetric dihydroxylation reaction. Several organometallic reagents were added to the aldehydes and the resulting adducts treated with H2-Pd/C to give diastereomerically and enantiomerically enriched 1,2,3-triol-containing building blocks for asymmetric synthesis.

LanguageEnglish (US)
Pages9819-9826
Number of pages8
JournalTetrahedron
Volume48
Issue number45
DOIs
StatePublished - Jan 1 1992

Fingerprint

Stilbenes
Enantiomers
Organometallics
Aldehydes
diphenyl
1,4-dioxane
hydrobenzoin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

(2S, 3S, 5S)- and (2S, 3S, 5R)-5-carboxaldehyde-2,3-diphenyl-1,4-dioxane as surrogates for optically pure 2,3-O-isopropylideneglyceraldehyde in asymmetric synthesis. / Aubé, Jeffrey; Mossman, Craig J.; Dickey, Susan.

In: Tetrahedron, Vol. 48, No. 45, 01.01.1992, p. 9819-9826.

Research output: Research - peer-reviewArticle

@article{6ddf0f1a2d2e4a4c99e099d801e04869,
title = "(2S, 3S, 5S)- and (2S, 3S, 5R)-5-carboxaldehyde-2,3-diphenyl-1,4-dioxane as surrogates for optically pure 2,3-O-isopropylideneglyceraldehyde in asymmetric synthesis",
abstract = "The title compounds were prepared from threo-hydrobenzoin, either enantiomer of which is readily available from trans-stilbene using the Sharpless asymmetric dihydroxylation reaction. Several organometallic reagents were added to the aldehydes and the resulting adducts treated with H2-Pd/C to give diastereomerically and enantiomerically enriched 1,2,3-triol-containing building blocks for asymmetric synthesis.",
author = "Jeffrey Aubé and Mossman, {Craig J.} and Susan Dickey",
year = "1992",
month = "1",
doi = "10.1016/S0040-4020(01)92276-8",
volume = "48",
pages = "9819--9826",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "45",

}

TY - JOUR

T1 - (2S, 3S, 5S)- and (2S, 3S, 5R)-5-carboxaldehyde-2,3-diphenyl-1,4-dioxane as surrogates for optically pure 2,3-O-isopropylideneglyceraldehyde in asymmetric synthesis

AU - Aubé,Jeffrey

AU - Mossman,Craig J.

AU - Dickey,Susan

PY - 1992/1/1

Y1 - 1992/1/1

N2 - The title compounds were prepared from threo-hydrobenzoin, either enantiomer of which is readily available from trans-stilbene using the Sharpless asymmetric dihydroxylation reaction. Several organometallic reagents were added to the aldehydes and the resulting adducts treated with H2-Pd/C to give diastereomerically and enantiomerically enriched 1,2,3-triol-containing building blocks for asymmetric synthesis.

AB - The title compounds were prepared from threo-hydrobenzoin, either enantiomer of which is readily available from trans-stilbene using the Sharpless asymmetric dihydroxylation reaction. Several organometallic reagents were added to the aldehydes and the resulting adducts treated with H2-Pd/C to give diastereomerically and enantiomerically enriched 1,2,3-triol-containing building blocks for asymmetric synthesis.

UR - http://www.scopus.com/inward/record.url?scp=0026489676&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026489676&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)92276-8

DO - 10.1016/S0040-4020(01)92276-8

M3 - Article

VL - 48

SP - 9819

EP - 9826

JO - Tetrahedron

T2 - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 45

ER -