Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication

Wolfgang Oppolzer; Mark Kurth; Daniel Reichlin; Christian Chapuis; Martin Mohnhaupt; Frank Moffatt

doi:10.1002/hlca.19810640841

Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication

Wolfgang Oppolzer, Mark Kurth, Daniel Reichlin, Christian Chapuis, Martin Mohnhaupt, Frank Moffatt

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

125 Scopus citations

Abstract

Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl₄‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.

Original language	German
Pages (from-to)	2802-2807
Number of pages	6
Journal	Helvetica Chimica Acta
Volume	64
Issue number	8
DOIs	https://doi.org/10.1002/hlca.19810640841
State	Published - 1981
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication",

abstract = "Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.",

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year = "1981",

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T1 - Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication

AU - Oppolzer, Wolfgang

AU - Kurth, Mark

AU - Reichlin, Daniel

AU - Chapuis, Christian

AU - Mohnhaupt, Martin

AU - Moffatt, Frank

PY - 1981

Y1 - 1981

N2 - Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.

AB - Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.

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Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication

Abstract

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