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Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates.
Org Lett. 2010 Feb 19; 12(4):720-3.OL

Abstract

The direct asymmetric allylic alkylation of beta,gamma-butenolides with MBH carbonates to access gamma,gamma-disubstituted butenolides containing adjacent quaternary and tertiary chiral centers has been presented in excellent stereoselectivities (86-96% ee, dr >95:5) and moderate to good yield (50-83%). Their synthetic utility has been well demonstrated by the facile construction of bicyclic lactones bearing 4-5 stereogenic centers.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Cui HL
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, China.
Huang JR
No affiliation info available
Lei J
No affiliation info available
Wang ZF
No affiliation info available
Chen S
No affiliation info available
Wu L
No affiliation info available
Chen YC
No affiliation info available

MeSH

4-ButyrolactoneAlkylationAllyl CompoundsCarbonatesCatalysisCinchona AlkaloidsCombinatorial Chemistry TechniquesMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20104883

Citation

Cui, Hai-Lei, et al. "Direct Asymmetric Allylic Alkylation of Butenolides With Morita-Baylis-Hillman Carbonates." Organic Letters, vol. 12, no. 4, 2010, pp. 720-3.
Cui HL, Huang JR, Lei J, et al. Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates. Org Lett. 2010;12(4):720-3.
Cui, H. L., Huang, J. R., Lei, J., Wang, Z. F., Chen, S., Wu, L., & Chen, Y. C. (2010). Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates. Organic Letters, 12(4), 720-3. https://doi.org/10.1021/ol100014m
Cui HL, et al. Direct Asymmetric Allylic Alkylation of Butenolides With Morita-Baylis-Hillman Carbonates. Org Lett. 2010 Feb 19;12(4):720-3. PubMed PMID: 20104883.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric allylic alkylation of butenolides with Morita-Baylis-Hillman carbonates. AU - Cui,Hai-Lei, AU - Huang,Ji-Rong, AU - Lei,Jie, AU - Wang,Zhao-Feng, AU - Chen,Shi, AU - Wu,Li, AU - Chen,Ying-Chun, PY - 2010/1/29/entrez PY - 2010/1/29/pubmed PY - 2010/3/12/medline SP - 720 EP - 3 JF - Organic letters JO - Org Lett VL - 12 IS - 4 N2 - The direct asymmetric allylic alkylation of beta,gamma-butenolides with MBH carbonates to access gamma,gamma-disubstituted butenolides containing adjacent quaternary and tertiary chiral centers has been presented in excellent stereoselectivities (86-96% ee, dr >95:5) and moderate to good yield (50-83%). Their synthetic utility has been well demonstrated by the facile construction of bicyclic lactones bearing 4-5 stereogenic centers. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20104883/Direct_asymmetric_allylic_alkylation_of_butenolides_with_Morita_Baylis_Hillman_carbonates_ L2 - https://doi.org/10.1021/ol100014m DB - PRIME DP - Unbound Medicine ER -