Reagent-Controlled Asymmetric Homologation of Boronic Esters by Enantioenriched Main-Group Chiral Carbenoids

Putative enantioenriched carbenoid species, (R)-1-chloro-2-phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (−)-(R S,R)-1-chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 4; pp. 773 - 776
Main Authors Blakemore, Paul R, Marsden, Stephen P, Vater, Huw D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.02.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
INSERTION
GENERATION
CARBANIONS
EFFICIENT
GRIGNARD-REAGENTS
1-CHLOROALKYL PHENYL SULFOXIDES
CONFIGURATIONAL STABILITY
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Summary:Putative enantioenriched carbenoid species, (R)-1-chloro-2-phenylethylmagnesium chloride (9) and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (−)-(R S,R)-1-chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol053055k