Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids

Elena Díez; Darren J. Dixon; Steven V. Ley

doi:10.1002/1521-3773(20010803)40:15<2906::AID- ANIE2906>3.0.CO;2-5

Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids

Elena Díez
, Darren J. Dixon
, Steven V. Ley

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

Abstract

According to a chiral memory protocol, a chiral glycolic acid equivalent, the butane-2,3-diacetal-desymmetrized glycolate 2, is obtained from chiral 3-halopropane-1,2-diols 1. Compound 2 is a new and effective building block for the synthesis of mono- and dialkylated α-hydroxy acids 3, which constitute a biologically and pharmacologically important structural motif.

Original language	English
Pages (from-to)	2906-2909
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	15
DOIs	https://doi.org/10.1002/1521-3773(20010803)40:15<2906::AID- ANIE2906>3.0.CO;2-5
Publication status	Published - 3 Aug 2001

Keywords

α-hydroxy acids
Alkylation
Asymmetric synthesis
Chiral memory
Diastereoselectivity

Access to Document

10.1002/1521-3773(20010803)40:15<2906::AID- ANIE2906>3.0.CO;2-5

Cite this

@article{5afad470a0e84780a508815b0c83b7b0,

title = "Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids",

abstract = "According to a chiral memory protocol, a chiral glycolic acid equivalent, the butane-2,3-diacetal-desymmetrized glycolate 2, is obtained from chiral 3-halopropane-1,2-diols 1. Compound 2 is a new and effective building block for the synthesis of mono- and dialkylated α-hydroxy acids 3, which constitute a biologically and pharmacologically important structural motif.",

keywords = "α-hydroxy acids, Alkylation, Asymmetric synthesis, Chiral memory, Diastereoselectivity",

author = "Elena D{\'i}ez and Dixon, \{Darren J.\} and Ley, \{Steven V.\}",

year = "2001",

month = aug,

day = "3",

doi = "10.1002/1521-3773(20010803)40:15<2906::AID- ANIE2906>3.0.CO;2-5",

language = "English",

volume = "40",

pages = "2906--2909",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons Ltd",

number = "15",

}

TY - JOUR

T1 - Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids

AU - Díez, Elena

AU - Dixon, Darren J.

AU - Ley, Steven V.

PY - 2001/8/3

Y1 - 2001/8/3

N2 - According to a chiral memory protocol, a chiral glycolic acid equivalent, the butane-2,3-diacetal-desymmetrized glycolate 2, is obtained from chiral 3-halopropane-1,2-diols 1. Compound 2 is a new and effective building block for the synthesis of mono- and dialkylated α-hydroxy acids 3, which constitute a biologically and pharmacologically important structural motif.

AB - According to a chiral memory protocol, a chiral glycolic acid equivalent, the butane-2,3-diacetal-desymmetrized glycolate 2, is obtained from chiral 3-halopropane-1,2-diols 1. Compound 2 is a new and effective building block for the synthesis of mono- and dialkylated α-hydroxy acids 3, which constitute a biologically and pharmacologically important structural motif.

KW - α-hydroxy acids

KW - Alkylation

KW - Asymmetric synthesis

KW - Chiral memory

KW - Diastereoselectivity

U2 - 10.1002/1521-3773(20010803)40:15<2906::AID- ANIE2906>3.0.CO;2-5

DO - 10.1002/1521-3773(20010803)40:15<2906::AID- ANIE2906>3.0.CO;2-5

M3 - Article

SN - 1433-7851

VL - 40

SP - 2906

EP - 2909

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids

Abstract

Keywords

Access to Document

Fingerprint

Cite this