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Organic Letters

Organic Letters

IF: 4.9
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Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate

Published:10 August 2012 DOI: 10.1021/ol301782s PMID: 22880620
P. Veeraraghavan Ramachandran*, Prem B. Chanda

Abstract

Unlike the enolboration–aldolization of methyl propanoate, the choice of either the solvent or temperature determines the diastereoselectivity during the enolboration–aldolization of methyl phenylacetate. In CH2Cl2, the reaction favors the anti-pathway at ?78 °C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.

Substances (2)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Dichloromethane 75-09-2 CH2Cl2 1289 suppliers $8660.00
Methyl phenylacetate 101-41-7 C9H10O2 579 suppliers $16.80-$669.00

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