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Highly enantioselective mukaiyama aldol reactions catalyzed by a chiral oxazaborolidinium ion: total synthesis of (-)-inthomycin C.
Org Lett. 2010 Nov 19; 12(22):5088-91.OL

Abstract

A cationic oxazaborolidinium-catalyzed asymmetric Mukaiyama aldol reaction of (1-methoxy-2-methyl-propenyloxy)-trimethylsilane with various aldehydes including α,β-disubstituted acroleins has been developed in high yields and enantioselectivities. The synthetic utility of this methodology was demonstrated in the first short synthesis of naturally occurring inthomycin C in high enantiopurity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Senapati BK
Department of Chemistry, Sungkyunkwan University, Suwon, 440-746, Korea.
Gao L
No affiliation info available
Lee SI
No affiliation info available
Hwang GS
No affiliation info available
Ryu DH
No affiliation info available

MeSH

AldehydesBiological ProductsBoron CompoundsCatalysisCombinatorial Chemistry TechniquesMolecular StructureOxazolesSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20958087

Citation

Senapati, Bidyut Kumar, et al. "Highly Enantioselective Mukaiyama Aldol Reactions Catalyzed By a Chiral Oxazaborolidinium Ion: Total Synthesis of (-)-inthomycin C." Organic Letters, vol. 12, no. 22, 2010, pp. 5088-91.
Senapati BK, Gao L, Lee SI, et al. Highly enantioselective mukaiyama aldol reactions catalyzed by a chiral oxazaborolidinium ion: total synthesis of (-)-inthomycin C. Org Lett. 2010;12(22):5088-91.
Senapati, B. K., Gao, L., Lee, S. I., Hwang, G. S., & Ryu, D. H. (2010). Highly enantioselective mukaiyama aldol reactions catalyzed by a chiral oxazaborolidinium ion: total synthesis of (-)-inthomycin C. Organic Letters, 12(22), 5088-91. https://doi.org/10.1021/ol102234k
Senapati BK, et al. Highly Enantioselective Mukaiyama Aldol Reactions Catalyzed By a Chiral Oxazaborolidinium Ion: Total Synthesis of (-)-inthomycin C. Org Lett. 2010 Nov 19;12(22):5088-91. PubMed PMID: 20958087.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective mukaiyama aldol reactions catalyzed by a chiral oxazaborolidinium ion: total synthesis of (-)-inthomycin C. AU - Senapati,Bidyut Kumar, AU - Gao,Lizhu, AU - Lee,Sung Il, AU - Hwang,Geum-Sook, AU - Ryu,Do Hyun, Y1 - 2010/10/19/ PY - 2010/10/21/entrez PY - 2010/10/21/pubmed PY - 2011/1/15/medline SP - 5088 EP - 91 JF - Organic letters JO - Org Lett VL - 12 IS - 22 N2 - A cationic oxazaborolidinium-catalyzed asymmetric Mukaiyama aldol reaction of (1-methoxy-2-methyl-propenyloxy)-trimethylsilane with various aldehydes including α,β-disubstituted acroleins has been developed in high yields and enantioselectivities. The synthetic utility of this methodology was demonstrated in the first short synthesis of naturally occurring inthomycin C in high enantiopurity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20958087/Highly_enantioselective_mukaiyama_aldol_reactions_catalyzed_by_a_chiral_oxazaborolidinium_ion:_total_synthesis_of_____inthomycin_C_ L2 - https://doi.org/10.1021/ol102234k DB - PRIME DP - Unbound Medicine ER -