Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones

Stephen G. Davies; Rebecca L. Nicholson; Andrew D. Smith

doi:10.1039/b411724g

Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones

Stephen G. Davies^*
, Rebecca L. Nicholson
, Andrew D. Smith

^*Corresponding author for this work

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

Abstract

Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral α,β-dihydroxy- or α,β-γ-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

Original language	English
Pages (from-to)	3385-3400
Number of pages	16
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	22
DOIs	https://doi.org/10.1039/b411724g
Publication status	Published - 21 Nov 2004

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title = "Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones",

abstract = "Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral α,β-dihydroxy- or α,β-γ-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.",

author = "Davies, \{Stephen G.\} and Nicholson, \{Rebecca L.\} and Smith, \{Andrew D.\}",

year = "2004",

month = nov,

day = "21",

doi = "10.1039/b411724g",

language = "English",

volume = "2",

pages = "3385--3400",

journal = "Organic and Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

number = "22",

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TY - JOUR

T1 - Double diastereoselective SuperQuat glycolate aldol reactions

T2 - Application to the asymmetric synthesis of polyfunctionalised lactones

AU - Davies, Stephen G.

AU - Nicholson, Rebecca L.

AU - Smith, Andrew D.

PY - 2004/11/21

Y1 - 2004/11/21

N2 - Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral α,β-dihydroxy- or α,β-γ-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

AB - Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral α,β-dihydroxy- or α,β-γ-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

UR - https://www.scopus.com/pages/publications/10244241903

U2 - 10.1039/b411724g

DO - 10.1039/b411724g

M3 - Article

C2 - 15534718

AN - SCOPUS:10244241903

SN - 1477-0520

VL - 2

SP - 3385

EP - 3400

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 22

ER -

Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones

Abstract

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