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Asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis.
Org Lett. 2009 Oct 15; 11(20):4660-3.OL

Abstract

The first chemo- and alpha-regioselective asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins has been presented in excellent diastereo- and enantioselectivities (dr up to >99:1, 93-96% ee) via dienamine catalysis. The Michael adducts have been efficiently converted to a number of optically pure cyclic frameworks with versatile scaffold diversity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Han B
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Xiao YC
No affiliation info available
He ZQ
No affiliation info available
Chen YC
No affiliation info available

MeSH

AldehydesAlkenesAminesCatalysisCrystallography, X-RayStereoisomerismSubstrate Specificity

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19754072

Citation

Han, Bo, et al. "Asymmetric Michael Addition of Gamma,gamma-disubstituted Alpha,beta-unsaturated Aldehydes to Nitroolefins Via Dienamine Catalysis." Organic Letters, vol. 11, no. 20, 2009, pp. 4660-3.
Han B, Xiao YC, He ZQ, et al. Asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis. Org Lett. 2009;11(20):4660-3.
Han, B., Xiao, Y. C., He, Z. Q., & Chen, Y. C. (2009). Asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis. Organic Letters, 11(20), 4660-3. https://doi.org/10.1021/ol901939b
Han B, et al. Asymmetric Michael Addition of Gamma,gamma-disubstituted Alpha,beta-unsaturated Aldehydes to Nitroolefins Via Dienamine Catalysis. Org Lett. 2009 Oct 15;11(20):4660-3. PubMed PMID: 19754072.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins via dienamine catalysis. AU - Han,Bo, AU - Xiao,You-Cai, AU - He,Zhao-Quan, AU - Chen,Ying-Chun, PY - 2009/9/17/entrez PY - 2009/9/17/pubmed PY - 2009/12/23/medline SP - 4660 EP - 3 JF - Organic letters JO - Org Lett VL - 11 IS - 20 N2 - The first chemo- and alpha-regioselective asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins has been presented in excellent diastereo- and enantioselectivities (dr up to >99:1, 93-96% ee) via dienamine catalysis. The Michael adducts have been efficiently converted to a number of optically pure cyclic frameworks with versatile scaffold diversity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19754072/Asymmetric_Michael_addition_of_gammagamma_disubstituted_alphabeta_unsaturated_aldehydes_to_nitroolefins_via_dienamine_catalysis_ L2 - https://doi.org/10.1021/ol901939b DB - PRIME DP - Unbound Medicine ER -