Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids.J Am Chem Soc. 2003 Oct 08; 125(40):12094-5.JA
Abstract
Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39-88%) and high enantioselectivities (67-96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes.
Pub Type(s)
Journal Article
Language
eng
PubMed ID
14518986
Citation
McDougal, Nolan T., and Scott E. Schaus. "Asymmetric Morita-Baylis-Hillman Reactions Catalyzed By Chiral Brønsted Acids." Journal of the American Chemical Society, vol. 125, no. 40, 2003, pp. 12094-5.
McDougal NT, Schaus SE. Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids. J Am Chem Soc. 2003;125(40):12094-5.
McDougal, N. T., & Schaus, S. E. (2003). Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids. Journal of the American Chemical Society, 125(40), 12094-5.
McDougal NT, Schaus SE. Asymmetric Morita-Baylis-Hillman Reactions Catalyzed By Chiral Brønsted Acids. J Am Chem Soc. 2003 Oct 8;125(40):12094-5. PubMed PMID: 14518986.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Brønsted acids.
AU - McDougal,Nolan T,
AU - Schaus,Scott E,
PY - 2003/10/2/pubmed
PY - 2003/10/2/medline
PY - 2003/10/2/entrez
SP - 12094
EP - 5
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 125
IS - 40
N2 - Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita-Baylis-Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2-20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39-88%) and high enantioselectivities (67-96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes.
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/14518986/Asymmetric_Morita_Baylis_Hillman_reactions_catalyzed_by_chiral_Br��nsted_acids_
DB - PRIME
DP - Unbound Medicine
ER -
