Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone

Neil Barnwell; Andrew Watts; Lindsay Purdie; Duncan M. Gill

doi:10.1016/j.tetlet.2012.02.008

Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone

Neil Barnwell, Andrew Watts, Lindsay Purdie, Duncan M. Gill

AstraZeneca

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

5 Citations (Scopus)

Abstract

A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates.

Original language	English
Pages (from-to)	1951-1953
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	15
Early online date	10 Feb 2012
DOIs	https://doi.org/10.1016/j.tetlet.2012.02.008
Publication status	Published - 11 Apr 2012
Externally published	Yes

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title = "Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone",

abstract = "A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates.",

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AU - Barnwell, Neil

AU - Watts, Andrew

AU - Purdie, Lindsay

AU - Gill, Duncan M.

PY - 2012/4/11

Y1 - 2012/4/11

N2 - A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates.

AB - A diastereoselective Strecker reaction using (R)-(-)-phenylglycinol forms the basis of a concise scalemic route to dialkylhydantoin 1. The phenylglycinol functionality was exploited in the manipulation of the aminonitrile Strecker product through to the dialkylhydantoin via a short, efficient sequence involving crystalline intermediates.

KW - Asymmetric

KW - Hydantoin

KW - Stereoselective synthesis

KW - Strecker reaction

UR - https://www.scopus.com/pages/publications/84858159277

U2 - 10.1016/j.tetlet.2012.02.008

DO - 10.1016/j.tetlet.2012.02.008

M3 - Article

AN - SCOPUS:84858159277

SN - 0040-4039

VL - 53

SP - 1951

EP - 1953

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Stereoselective synthesis of a dialkylhydantoin featuring an asymmetric Strecker reaction on an acyclic dialkyl ketone

Abstract

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