Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations.J Am Chem Soc. 2003 Apr 23; 125(16):4690-1.JA
Abstract
A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.
Pub Type(s)
Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.
Language
eng
PubMed ID
12696870
Citation
Murphy, Kerry E., and Amir H. Hoveyda. "Enantioselective Synthesis of Alpha-alkyl-beta,gamma-unsaturated Esters Through Efficient Cu-catalyzed Allylic Alkylations." Journal of the American Chemical Society, vol. 125, no. 16, 2003, pp. 4690-1.
Murphy KE, Hoveyda AH. Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations. J Am Chem Soc. 2003;125(16):4690-1.
Murphy, K. E., & Hoveyda, A. H. (2003). Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations. Journal of the American Chemical Society, 125(16), 4690-1.
Murphy KE, Hoveyda AH. Enantioselective Synthesis of Alpha-alkyl-beta,gamma-unsaturated Esters Through Efficient Cu-catalyzed Allylic Alkylations. J Am Chem Soc. 2003 Apr 23;125(16):4690-1. PubMed PMID: 12696870.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations.
AU - Murphy,Kerry E,
AU - Hoveyda,Amir H,
PY - 2003/4/17/pubmed
PY - 2003/6/17/medline
PY - 2003/4/17/entrez
SP - 4690
EP - 1
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 125
IS - 16
N2 - A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/12696870/Enantioselective_synthesis_of_alpha_alkyl_betagamma_unsaturated_esters_through_efficient_cu_catalyzed_allylic_alkylations_
DB - PRIME
DP - Unbound Medicine
ER -
