Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction.Org Lett. 2005 Sep 01; 7(18):3849-51.OL
Abstract
The intramolecular Morita-Baylis-Hillman (MBH) reaction has been achieved with unprecedented levels of enantioselectivity. Using a co-catalyst system involving pipecolinic acid and N-methylimidazole, cyclic MBH products have been obtained with enantiomer ratios of 92:8 (84% ee). In addition, reactions may be carried out with a "kinetic resolution quench" involving acetic anhydride and an asymmetric acylation catalyst such that ee enhancement occurs to deliver products with >98% ee with an isolated yield of 50%. [reaction: see text]
Pub Type(s)
Journal Article
Language
eng
PubMed ID
16119914
Citation
Aroyan, Carrie E., et al. "Dual Catalyst Control in the Enantioselective Intramolecular Morita-Baylis-Hillman Reaction." Organic Letters, vol. 7, no. 18, 2005, pp. 3849-51.
Aroyan CE, Vasbinder MM, Miller SJ. Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction. Org Lett. 2005;7(18):3849-51.
Aroyan, C. E., Vasbinder, M. M., & Miller, S. J. (2005). Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction. Organic Letters, 7(18), 3849-51.
Aroyan CE, Vasbinder MM, Miller SJ. Dual Catalyst Control in the Enantioselective Intramolecular Morita-Baylis-Hillman Reaction. Org Lett. 2005 Sep 1;7(18):3849-51. PubMed PMID: 16119914.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction.
AU - Aroyan,Carrie E,
AU - Vasbinder,Melissa M,
AU - Miller,Scott J,
PY - 2005/8/27/pubmed
PY - 2005/8/27/medline
PY - 2005/8/27/entrez
SP - 3849
EP - 51
JF - Organic letters
JO - Org Lett
VL - 7
IS - 18
N2 - The intramolecular Morita-Baylis-Hillman (MBH) reaction has been achieved with unprecedented levels of enantioselectivity. Using a co-catalyst system involving pipecolinic acid and N-methylimidazole, cyclic MBH products have been obtained with enantiomer ratios of 92:8 (84% ee). In addition, reactions may be carried out with a "kinetic resolution quench" involving acetic anhydride and an asymmetric acylation catalyst such that ee enhancement occurs to deliver products with >98% ee with an isolated yield of 50%. [reaction: see text]
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/16119914/Dual_catalyst_control_in_the_enantioselective_intramolecular_Morita_Baylis_Hillman_reaction_
DB - PRIME
DP - Unbound Medicine
ER -
