Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones

Michael Morgen; Sebastian Bretzke; Pengfei Li; Dirk Menche

doi:10.1021/ol101755m

Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones

Michael Morgen
, Sebastian Bretzke
, Pengfei Li
, Dirk Menche

Heidelberg University

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

63 Scopus citations

Abstract

An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines.

Original language	English
Pages (from-to)	4494-4497
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	20
DOIs	https://doi.org/10.1021/ol101755m
State	Published - 15 Oct 2010
Externally published	Yes

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10.1021/ol101755m

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abstract = "An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclization proceeds with excellent yield (up to 99\%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines.",

author = "Michael Morgen and Sebastian Bretzke and Pengfei Li and Dirk Menche",

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T1 - Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones

AU - Morgen, Michael

AU - Bretzke, Sebastian

AU - Li, Pengfei

AU - Menche, Dirk

PY - 2010/10/15

Y1 - 2010/10/15

N2 - An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines.

AB - An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines.

UR - https://www.scopus.com/pages/publications/77957826125

U2 - 10.1021/ol101755m

DO - 10.1021/ol101755m

M3 - 文章

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones

Abstract

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