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Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B.
Org Lett. 2016 01 15; 18(2):160-3.OL

Abstract

Chiral oxazaborolidinium ion-catalyzed asymmetric cyclopropanation of α- or α,β-substituted acroleins with α-alkyl-α-diazoesters has been developed. With this methodology, chiral functionalized cyclopropanes containing a quaternary stereogenic center were obtained with high to excellent enantioselectivities (up to >99% ee). The synthetic utility of optically enriched functionalized cyclopropane was demonstrated in the first total synthesis of (+)-hamavellone B, which establishes the absolute configuration of natural (+)-hamavellone B.

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Authors+Show Affiliations

Shim SY
Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
Kim JY
Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
Nam M
Western Seoul Center, Korea Basic Science Institute , Seoul 120-140, Korea.
Hwang GS
Western Seoul Center, Korea Basic Science Institute , Seoul 120-140, Korea.
Ryu DH
Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.

MeSH

CatalysisCrystallography, X-RayCyclopropanesMolecular ConformationMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

26719983

Citation

Shim, Su Yong, et al. "Enantioselective Cyclopropanation With α-Alkyl-α-diazoesters Catalyzed By Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B." Organic Letters, vol. 18, no. 2, 2016, pp. 160-3.
Shim SY, Kim JY, Nam M, et al. Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B. Org Lett. 2016;18(2):160-3.
Shim, S. Y., Kim, J. Y., Nam, M., Hwang, G. S., & Ryu, D. H. (2016). Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B. Organic Letters, 18(2), 160-3. https://doi.org/10.1021/acs.orglett.5b02970
Shim SY, et al. Enantioselective Cyclopropanation With α-Alkyl-α-diazoesters Catalyzed By Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B. Org Lett. 2016 01 15;18(2):160-3. PubMed PMID: 26719983.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B. AU - Shim,Su Yong, AU - Kim,Jae Yeon, AU - Nam,Miso, AU - Hwang,Geum-Sook, AU - Ryu,Do Hyun, Y1 - 2015/12/31/ PY - 2016/1/1/entrez PY - 2016/1/1/pubmed PY - 2016/6/4/medline SP - 160 EP - 3 JF - Organic letters JO - Org Lett VL - 18 IS - 2 N2 - Chiral oxazaborolidinium ion-catalyzed asymmetric cyclopropanation of α- or α,β-substituted acroleins with α-alkyl-α-diazoesters has been developed. With this methodology, chiral functionalized cyclopropanes containing a quaternary stereogenic center were obtained with high to excellent enantioselectivities (up to >99% ee). The synthetic utility of optically enriched functionalized cyclopropane was demonstrated in the first total synthesis of (+)-hamavellone B, which establishes the absolute configuration of natural (+)-hamavellone B. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26719983/Enantioselective_Cyclopropanation_with_α_Alkyl_α_diazoesters_Catalyzed_by_Chiral_Oxazaborolidinium_Ion:_Total_Synthesis_of__+__Hamavellone_B_ DB - PRIME DP - Unbound Medicine ER -