A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: A powerful tool for carbohydrate synthesis

Milan Bergeron-Brlek; Timothy Teoh; Robert Britton

doi:10.1021/ol401370b

A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: A powerful tool for carbohydrate synthesis

Milan Bergeron-Brlek
, Timothy Teoh
, Robert Britton

Simon Fraser University

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

57 Citations (Scopus)

Abstract

A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

Original language	English
Pages (from-to)	3554-3557
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	14
DOIs	https://doi.org/10.1021/ol401370b
Publication status	Published - 19 Jul 2013
Externally published	Yes

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title = "A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: A powerful tool for carbohydrate synthesis",

abstract = "A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.",

author = "Milan Bergeron-Brlek and Timothy Teoh and Robert Britton",

year = "2013",

month = jul,

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doi = "10.1021/ol401370b",

language = "English",

volume = "15",

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T1 - A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution

T2 - A powerful tool for carbohydrate synthesis

AU - Bergeron-Brlek, Milan

AU - Teoh, Timothy

AU - Britton, Robert

PY - 2013/7/19

Y1 - 2013/7/19

N2 - A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

AB - A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.

UR - https://www.scopus.com/pages/publications/84880562104

U2 - 10.1021/ol401370b

DO - 10.1021/ol401370b

M3 - Journal Article

C2 - 23819733

AN - SCOPUS:84880562104

SN - 1523-7060

VL - 15

SP - 3554

EP - 3557

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: A powerful tool for carbohydrate synthesis

Abstract

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