Alkene metathesis approach to β-unsubstituted anti -allylic alcohols and their use in ene-yne metathesis

Joseph R. Clark; Jonathan M. French; Steven T. Diver

doi:10.1021/jo202398q

Alkene metathesis approach to β-unsubstituted anti -allylic alcohols and their use in ene-yne metathesis

Joseph R. Clark
, Jonathan M. French
, Steven T. Diver

Chemistry

SUNY Buffalo

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

14 Scopus citations

Abstract

The synthesis of β-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a β-alkenyl group, which facilitated the aldol step. The β-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.

Original language	English
Pages (from-to)	1599-1604
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	77
Issue number	3
DOIs	https://doi.org/10.1021/jo202398q
State	Published - Feb 3 2012

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title = "Alkene metathesis approach to β-unsubstituted anti -allylic alcohols and their use in ene-yne metathesis",

abstract = "The synthesis of β-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a β-alkenyl group, which facilitated the aldol step. The β-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.",

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journal = "Journal of Organic Chemistry",

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T1 - Alkene metathesis approach to β-unsubstituted anti -allylic alcohols and their use in ene-yne metathesis

AU - Clark, Joseph R.

AU - French, Jonathan M.

AU - Diver, Steven T.

PY - 2012/2/3

Y1 - 2012/2/3

N2 - The synthesis of β-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a β-alkenyl group, which facilitated the aldol step. The β-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.

AB - The synthesis of β-unsubstituted, anti-allylic alcohols using a catalytic Evans aldol reaction conjoined with a relay-type ring-closing alkene metathesis is reported. The metathesis step serves to remove a β-alkenyl group, which facilitated the aldol step. The β-substituted enals serve as acrolein surrogates. The products were employed in ene-yne cross metathesis.

UR - https://www.scopus.com/pages/publications/84856657302

U2 - 10.1021/jo202398q

DO - 10.1021/jo202398q

M3 - Article

AN - SCOPUS:84856657302

SN - 0022-3263

VL - 77

SP - 1599

EP - 1604

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Alkene metathesis approach to β-unsubstituted anti -allylic alcohols and their use in ene-yne metathesis

Abstract

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