Organocatalyzed Rearrangement of S-(2-Oxoalkyl)-thioenoates

David M. Leace; Matthew R. Straub; Benjamin A. Matz; Vladimir B. Birman

doi:10.1021/acs.joc.9b00925

Organocatalyzed Rearrangement of S-(2-Oxoalkyl)-thioenoates

David M. Leace
, Matthew R. Straub
, Benjamin A. Matz
, Vladimir B. Birman

Department of Chemistry

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

8 Scopus citations

Abstract

The highly Lewis basic amidine-based catalyst DHIP promotes the rearrangement of S-phenacyl thiocinnamate and related thioesters into dihydrothiophene derivatives. In contrast to previously explored rearrangements of thioesters, the reaction proceeds via a novel Dieckmann-like cyclization pathway. An alternative two-component synthesis of the same products has also been developed.

Original language	English
Pages (from-to)	7523-7531
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	84
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.9b00925
State	Published - Jun 7 2019

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title = "Organocatalyzed Rearrangement of S-(2-Oxoalkyl)-thioenoates",

abstract = "The highly Lewis basic amidine-based catalyst DHIP promotes the rearrangement of S-phenacyl thiocinnamate and related thioesters into dihydrothiophene derivatives. In contrast to previously explored rearrangements of thioesters, the reaction proceeds via a novel Dieckmann-like cyclization pathway. An alternative two-component synthesis of the same products has also been developed.",

author = "Leace, \{David M.\} and Straub, \{Matthew R.\} and Matz, \{Benjamin A.\} and Birman, \{Vladimir B.\}",

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doi = "10.1021/acs.joc.9b00925",

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AU - Leace, David M.

AU - Straub, Matthew R.

AU - Matz, Benjamin A.

AU - Birman, Vladimir B.

PY - 2019/6/7

Y1 - 2019/6/7

N2 - The highly Lewis basic amidine-based catalyst DHIP promotes the rearrangement of S-phenacyl thiocinnamate and related thioesters into dihydrothiophene derivatives. In contrast to previously explored rearrangements of thioesters, the reaction proceeds via a novel Dieckmann-like cyclization pathway. An alternative two-component synthesis of the same products has also been developed.

AB - The highly Lewis basic amidine-based catalyst DHIP promotes the rearrangement of S-phenacyl thiocinnamate and related thioesters into dihydrothiophene derivatives. In contrast to previously explored rearrangements of thioesters, the reaction proceeds via a novel Dieckmann-like cyclization pathway. An alternative two-component synthesis of the same products has also been developed.

UR - https://www.scopus.com/pages/publications/85066915462

U2 - 10.1021/acs.joc.9b00925

DO - 10.1021/acs.joc.9b00925

M3 - Article

C2 - 31099563

AN - SCOPUS:85066915462

SN - 0022-3263

VL - 84

SP - 7523

EP - 7531

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Organocatalyzed Rearrangement of S-(2-Oxoalkyl)-thioenoates

Abstract

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