Lewis base activation of Lewis acids. Vinylogous aldol reactions.J Am Chem Soc. 2003 Jul 02; 125(26):7800-1.JA
Abstract
A highly regioselective vinylogous aldol reaction catalyzed by SiCl4 and a chiral phosphoramide (R,R)-5, providing delta-hydroxy enones for a variety of aldehyde and dienol ether structures, has been developed. Low catalyst loadings (1 mol %) can be employed, giving the products in good yields, excellent enantioselectivities, and in some cases excellent anti diastereoselectivities. Both simple ester-derived dienol ethers as well as dioxanone-derived dienol ethers are employed. The observed regioselectivity is rationalized in terms of the sensitivity of the catalyst to the steric demands of the nucleophile.
Pub Type(s)
Journal Article
Language
eng
PubMed ID
12822988
Citation
Denmark, Scott E., and Gregory L. Beutner. "Lewis Base Activation of Lewis Acids. Vinylogous Aldol Reactions." Journal of the American Chemical Society, vol. 125, no. 26, 2003, pp. 7800-1.
Denmark SE, Beutner GL. Lewis base activation of Lewis acids. Vinylogous aldol reactions. J Am Chem Soc. 2003;125(26):7800-1.
Denmark, S. E., & Beutner, G. L. (2003). Lewis base activation of Lewis acids. Vinylogous aldol reactions. Journal of the American Chemical Society, 125(26), 7800-1.
Denmark SE, Beutner GL. Lewis Base Activation of Lewis Acids. Vinylogous Aldol Reactions. J Am Chem Soc. 2003 Jul 2;125(26):7800-1. PubMed PMID: 12822988.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Lewis base activation of Lewis acids. Vinylogous aldol reactions.
AU - Denmark,Scott E,
AU - Beutner,Gregory L,
PY - 2003/6/26/pubmed
PY - 2003/6/26/medline
PY - 2003/6/26/entrez
SP - 7800
EP - 1
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 125
IS - 26
N2 - A highly regioselective vinylogous aldol reaction catalyzed by SiCl4 and a chiral phosphoramide (R,R)-5, providing delta-hydroxy enones for a variety of aldehyde and dienol ether structures, has been developed. Low catalyst loadings (1 mol %) can be employed, giving the products in good yields, excellent enantioselectivities, and in some cases excellent anti diastereoselectivities. Both simple ester-derived dienol ethers as well as dioxanone-derived dienol ethers are employed. The observed regioselectivity is rationalized in terms of the sensitivity of the catalyst to the steric demands of the nucleophile.
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/12822988/Lewis_base_activation_of_Lewis_acids__Vinylogous_aldol_reactions_
DB - PRIME
DP - Unbound Medicine
ER -
