Asymmetric catalytic aza-Morita-Baylis-Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction.Chem Commun (Camb). 2008 Dec 07CC
Abstract
A highly efficient aza-Morita-Baylis-Hillman reaction (aza-MBH reaction) of N-tosyl salicylaldehyde imines with alpha,beta-unsaturated ketones has been achieved by using beta-isocupreidine (beta-) as the catalyst (10 mol%) to give the corresponding adducts in good to high yields (90%-quant.) and excellent ee's (up to 99% ee), with adducts showing the opposite absolute configuration to that of those obtained in the similar aza-MBH reaction of N-tosyl aldimines with alpha,beta-unsaturated ketones.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
19030574
Citation
Shi, Min, et al. "Asymmetric Catalytic aza-Morita-Baylis-Hillman Reaction (aza-MBH): an Interesting Functional Group-caused Reversal of Asymmetric Induction." Chemical Communications (Cambridge, England), 2008, pp. 6025-7.
Shi M, Qi MJ, Liu XG. Asymmetric catalytic aza-Morita-Baylis-Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction. Chem Commun (Camb). 2008.
Shi, M., Qi, M. J., & Liu, X. G. (2008). Asymmetric catalytic aza-Morita-Baylis-Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction. Chemical Communications (Cambridge, England), (45), 6025-7. https://doi.org/10.1039/b814500h
Shi M, Qi MJ, Liu XG. Asymmetric Catalytic aza-Morita-Baylis-Hillman Reaction (aza-MBH): an Interesting Functional Group-caused Reversal of Asymmetric Induction. Chem Commun (Camb). 2008 Dec 7;(45)6025-7. PubMed PMID: 19030574.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Asymmetric catalytic aza-Morita-Baylis-Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction.
AU - Shi,Min,
AU - Qi,Ming-Juan,
AU - Liu,Xu-Guang,
Y1 - 2008/10/15/
PY - 2008/11/26/pubmed
PY - 2008/11/26/medline
PY - 2008/11/26/entrez
SP - 6025
EP - 7
JF - Chemical communications (Cambridge, England)
JO - Chem Commun (Camb)
IS - 45
N2 - A highly efficient aza-Morita-Baylis-Hillman reaction (aza-MBH reaction) of N-tosyl salicylaldehyde imines with alpha,beta-unsaturated ketones has been achieved by using beta-isocupreidine (beta-) as the catalyst (10 mol%) to give the corresponding adducts in good to high yields (90%-quant.) and excellent ee's (up to 99% ee), with adducts showing the opposite absolute configuration to that of those obtained in the similar aza-MBH reaction of N-tosyl aldimines with alpha,beta-unsaturated ketones.
SN - 1359-7345
UR - https://www.unboundmedicine.com/medline/citation/19030574/Asymmetric_catalytic_aza_Morita_Baylis_Hillman_reaction__aza_MBH_:_an_interesting_functional_group_caused_reversal_of_asymmetric_induction_
DB - PRIME
DP - Unbound Medicine
ER -
