Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4- epoxybutan-2-ol

José M. Concellón; Pablo L. Bernad; R. Alvarez; A. Rodríguez; B. Baragaña

doi:10.1016/S0040-4039(99)00313-5

Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4- epoxybutan-2-ol

José M. Concellón
, Pablo L. Bernad
, R. Alvarez
, A. Rodríguez
, B. Baragaña

Biological Chemistry and Drug Discovery

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

3 Citations (Scopus)

Abstract

(2S,3S)- And (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2- ol have been obtained with high diastereoselectivity by reduction of enantiopure (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2R,3S)- and (2S,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2- epoxybutane.

Original language	English
Pages (from-to)	2863-2864
Number of pages	2
Journal	Tetrahedron Letters
Volume	40
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(99)00313-5
Publication status	Published - 2 Apr 1999

Keywords

Chiral chloromethyl ketones
Diastereoselection
Reduction
β,γ-epoxy alcohols

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00313-5

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@article{227e2bfe64594398804118ce202927d4,

title = "Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4- epoxybutan-2-ol",

abstract = "(2S,3S)- And (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2- ol have been obtained with high diastereoselectivity by reduction of enantiopure (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2R,3S)- and (2S,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2- epoxybutane.",

keywords = "Chiral chloromethyl ketones, Diastereoselection, Reduction, β,γ-epoxy alcohols",

author = "Concell{\'o}n, \{Jos{\'e} M.\} and Bernad, \{Pablo L.\} and R. Alvarez and A. Rodr{\'i}guez and B. Baraga{\~n}a",

year = "1999",

month = apr,

day = "2",

doi = "10.1016/S0040-4039(99)00313-5",

language = "English",

volume = "40",

pages = "2863--2864",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "14",

}

TY - JOUR

T1 - Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4- epoxybutan-2-ol

AU - Concellón, José M.

AU - Bernad, Pablo L.

AU - Alvarez, R.

AU - Rodríguez, A.

AU - Baragaña, B.

PY - 1999/4/2

Y1 - 1999/4/2

N2 - (2S,3S)- And (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2- ol have been obtained with high diastereoselectivity by reduction of enantiopure (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2R,3S)- and (2S,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2- epoxybutane.

AB - (2S,3S)- And (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2- ol have been obtained with high diastereoselectivity by reduction of enantiopure (S)-3-[(tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2R,3S)- and (2S,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2- epoxybutane.

KW - Chiral chloromethyl ketones

KW - Diastereoselection

KW - Reduction

KW - β,γ-epoxy alcohols

UR - https://www.scopus.com/pages/publications/0033515791

U2 - 10.1016/S0040-4039(99)00313-5

DO - 10.1016/S0040-4039(99)00313-5

M3 - Article

AN - SCOPUS:0033515791

SN - 0040-4039

VL - 40

SP - 2863

EP - 2864

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Diastereoselective reduction of (S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2S,3R) and (2S,3S) O-tert-butyldimethylsilyl-3,4- epoxybutan-2-ol

Abstract

Keywords

ASJC Scopus subject areas

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