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Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts.
Chem Soc Rev. 2012 Jun 07; 41(11):4101-12.CS

Abstract

Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This tutorial review will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu TY
Department of Medicinal Chemistry, College of Pharmacy, The Third Military Medical University, Chongqing 400038, China.
Xie M
No affiliation info available
Chen YC
No affiliation info available

MeSH

AlkylationAminesCatalysisCyclizationLewis BasesPhosphinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22453359

Citation

Liu, Tian-Yu, et al. "Organocatalytic Asymmetric Transformations of Modified Morita-Baylis-Hillman Adducts." Chemical Society Reviews, vol. 41, no. 11, 2012, pp. 4101-12.
Liu TY, Xie M, Chen YC. Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts. Chem Soc Rev. 2012;41(11):4101-12.
Liu, T. Y., Xie, M., & Chen, Y. C. (2012). Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts. Chemical Society Reviews, 41(11), 4101-12. https://doi.org/10.1039/c2cs35017c
Liu TY, Xie M, Chen YC. Organocatalytic Asymmetric Transformations of Modified Morita-Baylis-Hillman Adducts. Chem Soc Rev. 2012 Jun 7;41(11):4101-12. PubMed PMID: 22453359.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts. AU - Liu,Tian-Yu, AU - Xie,Min, AU - Chen,Ying-Chun, Y1 - 2012/03/28/ PY - 2012/3/29/entrez PY - 2012/3/29/pubmed PY - 2012/9/11/medline SP - 4101 EP - 12 JF - Chemical Society reviews JO - Chem Soc Rev VL - 41 IS - 11 N2 - Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This tutorial review will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities. SN - 1460-4744 UR - https://www.unboundmedicine.com/medline/citation/22453359/Organocatalytic_asymmetric_transformations_of_modified_Morita_Baylis_Hillman_adducts_ DB - PRIME DP - Unbound Medicine ER -