Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters

David J. Buchanan; Darren J. Dixon; Felix A. Hernandez-Juan

doi:10.1021/ol049820x

Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters

David J. Buchanan
, Darren J. Dixon
, Felix A. Hernandez-Juan

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

Abstract

The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidene-malonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.

Original language	English
Pages (from-to)	1357-1360
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	9
DOIs	https://doi.org/10.1021/ol049820x
Publication status	Published - 29 Apr 2004

Keywords

Crystal structure; Molecular structure (of (methyltetrahydropyranyloxy)hydroxymethyl(methyl)pentanol); Asymmetric synthesis and induction (stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Michael reaction (stereoselective; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Esters Role: RCT (Reactant), RACT (Reactant or reagent) (a,b-unsatd.; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates)

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title = "Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters",

abstract = "The highly diastereoselective oxy-Michael addition of the {"}naked{"} anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidene-malonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.",

keywords = "Crystal structure; Molecular structure (of (methyltetrahydropyranyloxy)hydroxymethyl(methyl)pentanol); Asymmetric synthesis and induction (stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Michael reaction (stereoselective; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Esters Role: RCT (Reactant), RACT (Reactant or reagent) (a,b-unsatd.; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates)",

author = "Buchanan, \{David J.\} and Dixon, \{Darren J.\} and Hernandez-Juan, \{Felix A.\}",

year = "2004",

month = apr,

day = "29",

doi = "10.1021/ol049820x",

language = "English",

volume = "6",

pages = "1357--1360",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters

AU - Buchanan, David J.

AU - Dixon, Darren J.

AU - Hernandez-Juan, Felix A.

PY - 2004/4/29

Y1 - 2004/4/29

N2 - The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidene-malonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.

AB - The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidene-malonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.

KW - Crystal structure; Molecular structure (of (methyltetrahydropyranyloxy)hydroxymethyl(methyl)pentanol); Asymmetric synthesis and induction (stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahyd

U2 - 10.1021/ol049820x

DO - 10.1021/ol049820x

M3 - Article

SN - 1523-7052

VL - 6

SP - 1357

EP - 1360

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Highly stereoselective intermolecular oxy-michael addition reaction to α,β-unsaturated malonate esters

Abstract

Keywords

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