Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions.J Org Chem. 2003 Feb 07; 68(3):915-9.JO
Abstract
An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor, the reaction is complete within 20 min with high stereoselectivity and in reasonable chemical yields.
Pub Type(s)
Journal Article
Language
eng
PubMed ID
12558416
Citation
Yang, Kung-Shuo, et al. "Chiral Lewis Acid-catalyzed Asymmetric Baylis-Hillman Reactions." The Journal of Organic Chemistry, vol. 68, no. 3, 2003, pp. 915-9.
Yang KS, Lee WD, Pan JF, et al. Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions. J Org Chem. 2003;68(3):915-9.
Yang, K. S., Lee, W. D., Pan, J. F., & Chen, K. (2003). Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions. The Journal of Organic Chemistry, 68(3), 915-9.
Yang KS, et al. Chiral Lewis Acid-catalyzed Asymmetric Baylis-Hillman Reactions. J Org Chem. 2003 Feb 7;68(3):915-9. PubMed PMID: 12558416.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reactions.
AU - Yang,Kung-Shuo,
AU - Lee,Wei-Der,
AU - Pan,Jia-Fu,
AU - Chen,Kwunmin,
PY - 2003/2/1/pubmed
PY - 2003/2/1/medline
PY - 2003/2/1/entrez
SP - 915
EP - 9
JF - The Journal of organic chemistry
JO - J Org Chem
VL - 68
IS - 3
N2 - An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor, the reaction is complete within 20 min with high stereoselectivity and in reasonable chemical yields.
SN - 0022-3263
UR - https://www.unboundmedicine.com/medline/citation/12558416/Chiral_Lewis_acid_catalyzed_asymmetric_Baylis_Hillman_reactions_
DB - PRIME
DP - Unbound Medicine
ER -
