Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones

Shende Jiang; Gurdial Singh; Richard H. Wightman

Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones

Shende Jiang, Gurdial Singh, Richard H. Wightman

School of Engineering & Physical Sciences

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

11 Citations (Scopus)

Abstract

Reactions of organomagnesium and/or organolithium reagents with 2,3-O-isopropylidene-D-erythronolactone and 5-O-tertbutyldiphenylsilyl-2,3-O-isopropylidene-D-ribonolactone gave good yields of the corresponding hemiacetals which, by choice of hydride reagents, can be reduced stereoselectively to give products with a syn-(threo-) relationship between the new chiral centre and that at C-2 of the lactone.

Original language	English
Pages (from-to)	67-68
Number of pages	2
Journal	Chemistry Letters
Issue number	1
Publication status	Published - 1996

Cite this

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title = "Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones",

abstract = "Reactions of organomagnesium and/or organolithium reagents with 2,3-O-isopropylidene-D-erythronolactone and 5-O-tertbutyldiphenylsilyl-2,3-O-isopropylidene-D-ribonolactone gave good yields of the corresponding hemiacetals which, by choice of hydride reagents, can be reduced stereoselectively to give products with a syn-(threo-) relationship between the new chiral centre and that at C-2 of the lactone.",

author = "Shende Jiang and Gurdial Singh and Wightman, {Richard H.}",

year = "1996",

language = "English",

pages = "67--68",

journal = "Chemistry Letters",

issn = "1348-0715",

publisher = "Chemical Society of Japan",

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T1 - Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones

AU - Jiang, Shende

AU - Singh, Gurdial

AU - Wightman, Richard H.

PY - 1996

Y1 - 1996

N2 - Reactions of organomagnesium and/or organolithium reagents with 2,3-O-isopropylidene-D-erythronolactone and 5-O-tertbutyldiphenylsilyl-2,3-O-isopropylidene-D-ribonolactone gave good yields of the corresponding hemiacetals which, by choice of hydride reagents, can be reduced stereoselectively to give products with a syn-(threo-) relationship between the new chiral centre and that at C-2 of the lactone.

AB - Reactions of organomagnesium and/or organolithium reagents with 2,3-O-isopropylidene-D-erythronolactone and 5-O-tertbutyldiphenylsilyl-2,3-O-isopropylidene-D-ribonolactone gave good yields of the corresponding hemiacetals which, by choice of hydride reagents, can be reduced stereoselectively to give products with a syn-(threo-) relationship between the new chiral centre and that at C-2 of the lactone.

M3 - Article

SN - 1348-0715

SP - 67

EP - 68

JO - Chemistry Letters

JF - Chemistry Letters

IS - 1

ER -

Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones

Abstract

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