Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters

Darren J. Dixon; Steven V. Ley; Alessandra Polara; Tom Sheppard

doi:10.1021/ol016707n

Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters

Darren J. Dixon
, Steven V. Ley
, Alessandra Polara
, Tom Sheppard

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

Abstract

Figure presented The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

Original language	English
Pages (from-to)	3749-3752
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	23
DOIs	https://doi.org/10.1021/ol016707n
Publication status	Published - 15 Nov 2001

Keywords

Stereoselective synthesis (diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters); Aldehydes Role: RCT (Reactant), RACT (Reactant or reagent) (diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters); Aldol condensation (stereoselective; diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters)

Access to Document

10.1021/ol016707n

Cite this

@article{bb69f5f510a94f98a1f3578ea2bd01b7,

title = "Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters",

abstract = "Figure presented The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.",

keywords = "Stereoselective synthesis (diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters); Aldehydes Role: RCT (Reactant), RACT (Reactant or reagent) (diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters); Aldol condensation (stereoselective; diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters)",

author = "Dixon, \{Darren J.\} and Ley, \{Steven V.\} and Alessandra Polara and Tom Sheppard",

year = "2001",

month = nov,

day = "15",

doi = "10.1021/ol016707n",

language = "English",

volume = "3",

pages = "3749--3752",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters

AU - Dixon, Darren J.

AU - Ley, Steven V.

AU - Polara, Alessandra

AU - Sheppard, Tom

PY - 2001/11/15

Y1 - 2001/11/15

N2 - Figure presented The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

AB - Figure presented The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block 1 undergoes efficient and highly diastereoselective lithium enolate aldol reactions with both aromatic and aliphatic aldehydes to afford, after an acidic methanolysis deprotection step, the enantiopure anti-2,3-dihydroxy esters in good yield.

KW - Stereoselective synthesis (diastereoselective aldol of butanediacetal desymmetrized glycolic acid with aldehydes and deprotection of adducts to dihydroxy esters); Aldehydes Role: RCT (Reactant), RACT (Reactant or reagent) (diastereoselective aldol of buta

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/cc5yv42&sid=DataCite

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/cc5yv53&sid=DataCite

U2 - 10.1021/ol016707n

DO - 10.1021/ol016707n

M3 - Article

SN - 1523-7052

VL - 3

SP - 3749

EP - 3752

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this