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

doi:10.1080/00397918808064002

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

Chemistry & Biochemistry - Sci

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

12 Scopus citations

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 language	English (US)
Pages (from-to)	391-402
Number of pages	12
Journal	Synthetic Communications
Volume	18
Issue number	4
DOIs	https://doi.org/10.1080/00397918808064002
State	Published - Apr 1 1988

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397918808064002

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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.\}",

note = "Funding Information: Acknowledgement is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society, for support of this research. Partial support of this research by the American Heart Association, Arizona A f f i l i - ate, i s gratefully acknowledged.",

year = "1988",

month = apr,

day = "1",

doi = "10.1080/00397918808064002",

language = "English (US)",

volume = "18",

pages = "391--402",

journal = "Synthetic Communications",

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publisher = "Taylor and Francis Ltd.",

number = "4",

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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.

N1 - Funding Information: Acknowledgement is made to the donors of the Petroleum Research Fund, administered by the American Chemical Society, for support of this research. Partial support of this research by the American Heart Association, Arizona A f f i l i - ate, i s gratefully acknowledged.

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 - https://www.scopus.com/pages/publications/0041466697

UR - https://www.scopus.com/pages/publications/0041466697#tab=citedBy

U2 - 10.1080/00397918808064002

DO - 10.1080/00397918808064002

M3 - Article

AN - SCOPUS:0041466697

SN - 0039-7911

VL - 18

SP - 391

EP - 402

JO - Synthetic Communications

JF - Synthetic Communications

IS - 4

ER -

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

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