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.}",

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AU - Smith, Andrew D.

PY - 2004/11/21

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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.

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JO - Organic and Biomolecular Chemistry

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

Abstract

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