Document Detail

Metal-dependent reaction tuning with cyclopentylmetal reagents: application to the asymmetric synthesis of (+)-alpha-conhydrine and (S)-2-cyclopentyl-2-phenylglycolic acid.
MedLine Citation:
PMID:  19130529     Owner:  NLM     Status:  MEDLINE    
The reaction profile of the cyclopentyl organometallic reagents with the aliphatic ketones can be tuned to reduction or addition by changing the metal atom. Cyclopentylmagnesium bromide (CPMB) reduces aromatic and aliphatic aldehydes and ketones to the corresponding alcohols without any C-C bond formation and shows good diastereoselectivity in the reduction of the substituted cyclic and polycyclic ketones as well as chiral alpha-oxygenated aliphatic ketones. However, in the presence of 10 mol % of ZnCl(2), the cyclopentylmagnesium halides follow a normal Grignard addition to the ketones to give tertiary alcohols with complete diastereoselectivity. The reductive as well as the addition protocols were used for the asymmetric synthesis of two medicinally important compounds, (+)-alpha-conhydrine and (S)-2-cyclopentyl-2-phenylglycolic acid.
Siddharth Roy; Anubha Sharma; Soumyaditya Mula; Subrata Chattopadhyay
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  15     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2009  
Date Detail:
Created Date:  2009-02-02     Completed Date:  2009-03-04     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1713-22     Citation Subset:  IM    
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India.
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MeSH Terms
Aldehydes / chemistry
Cyclopentanes / chemical synthesis*
Glycolates / chemical synthesis*
Ketones / chemistry
Metals / chemistry
Organometallic Compounds / chemical synthesis*
Piperidines / chemical synthesis*
Reg. No./Substance:
0/(S)-2-cyclopentyl-2-phenylglycolic acid; 0/Aldehydes; 0/Cyclopentanes; 0/Glycolates; 0/Ketones; 0/Metals; 0/Organometallic Compounds; 0/Piperidines; 0/alpha-conhydrine; 0/cyclopentylmagnesium bromide

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