Homochiral ketals in organic synthesis. enantioselective synthesis of (4S,5S)-4,5-dihydroxycyclopent-2-en-1-one isopropylidine ketal

Christopher J. Flann, Eugene A Mash

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

: The title compound has been synthesized in 17% yield over six steps from 2-cyclopenten-l-one. The key step is catalytic osmylation of 4-bromo-?-cyclopenten-l-one 1,4-di-O-benzyl-D-threitol ketal to produce a chromatographically separable mixture of diastereomeric diols.

Original languageEnglish (US)
Pages (from-to)391-402
Number of pages12
JournalSynthetic Communications
Volume18
Issue number4
DOIs
StatePublished - Apr 1 1988

Fingerprint

threitol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Homochiral ketals in organic synthesis. enantioselective synthesis of (4S,5S)-4,5-dihydroxycyclopent-2-en-1-one isopropylidine ketal. / Flann, Christopher J.; Mash, Eugene A.

In: Synthetic Communications, Vol. 18, No. 4, 01.04.1988, p. 391-402.

Research output: Contribution to journalArticle

@article{5bbcb8057600438d994f5fe710fcdcba,
title = "Homochiral ketals in organic synthesis. enantioselective synthesis of (4S,5S)-4,5-dihydroxycyclopent-2-en-1-one isopropylidine ketal",
abstract = ": The title compound has been synthesized in 17{\%} yield over six steps from 2-cyclopenten-l-one. The key step is catalytic osmylation of 4-bromo-?-cyclopenten-l-one 1,4-di-O-benzyl-D-threitol ketal to produce a chromatographically separable mixture of diastereomeric diols.",
author = "Flann, {Christopher J.} and Mash, {Eugene A}",
year = "1988",
month = "4",
day = "1",
doi = "10.1080/00397918808064002",
language = "English (US)",
volume = "18",
pages = "391--402",
journal = "Synthetic Communications",
issn = "0039-7911",
publisher = "Taylor and Francis Ltd.",
number = "4",

}

TY - JOUR

T1 - Homochiral ketals in organic synthesis. enantioselective synthesis of (4S,5S)-4,5-dihydroxycyclopent-2-en-1-one isopropylidine ketal

AU - Flann, Christopher J.

AU - Mash, Eugene A

PY - 1988/4/1

Y1 - 1988/4/1

N2 - : The title compound has been synthesized in 17% yield over six steps from 2-cyclopenten-l-one. The key step is catalytic osmylation of 4-bromo-?-cyclopenten-l-one 1,4-di-O-benzyl-D-threitol ketal to produce a chromatographically separable mixture of diastereomeric diols.

AB - : The title compound has been synthesized in 17% yield over six steps from 2-cyclopenten-l-one. The key step is catalytic osmylation of 4-bromo-?-cyclopenten-l-one 1,4-di-O-benzyl-D-threitol ketal to produce a chromatographically separable mixture of diastereomeric diols.

UR - http://www.scopus.com/inward/record.url?scp=0041466697&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0041466697&partnerID=8YFLogxK

U2 - 10.1080/00397918808064002

DO - 10.1080/00397918808064002

M3 - Article

AN - SCOPUS:0041466697

VL - 18

SP - 391

EP - 402

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 4

ER -