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Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications
Leng, Dong-Hui1; Wang, De-Xiang1; Pan, Jie1; Huang, Zhi-Tang1; Wang, Mei-Xiang1,2
2009-08-21
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume74Issue:16Pages:6077-6082
AbstractCatalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst in neutral aqueous buffer at 30 degrees C, a number of racemic 1-benzylazetidine-2-carbonitriles, trans-1-benzyl-4-methylazetidine-2-carbonitrile. and 1-benzyl-2-methylazetidine-2-carbonitrile and their amide substrates underwent efficient and enantioselective biotransformations to afford the corresponding azetidine-2-carboxylic acids and their amide derivatives in excellent yields with cc up to >99.5%. The overall excellent, act enantioselectivity of the biocatalytic reactions stemmed from a combined effect of a very active but virtually nonenantioselective nitrite hydratase and a high R-enantioselective amidase involved in microbial whole cells. The synthetic applications have been demonstrated by the nucleophilic ring-opening reactions of azetidiniums of the resulting chiral azetidine-2-carbox amide derivatives for the preparation of alpha,gamma-diamino, alpha-phenoxy-gamma-amino, and alpha-cyano-gamma-amino carboxamides. The intramolecular Cul-catalyzed cross-coupling reaction for the synthesis of azetidine-fused 1,4-benzodiazepin-2-one derivative was also presented.
DOI10.1021/jo9011656
Indexed BySCI ; IC
Language英语
WOS IDWOS:000268907300038
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:30[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/68090
Collection中国科学院化学研究所
Corresponding AuthorWang, Mei-Xiang
Affiliation1.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
2.Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
Recommended Citation
GB/T 7714
Leng, Dong-Hui,Wang, De-Xiang,Pan, Jie,et al. Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications[J]. JOURNAL OF ORGANIC CHEMISTRY,2009,74(16):6077-6082.
APA Leng, Dong-Hui,Wang, De-Xiang,Pan, Jie,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2009).Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications.JOURNAL OF ORGANIC CHEMISTRY,74(16),6077-6082.
MLA Leng, Dong-Hui,et al."Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications".JOURNAL OF ORGANIC CHEMISTRY 74.16(2009):6077-6082.
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