Efficient Synthesis of cis‐3‐Substituted Prolines by Bidentate‐Assisted Palladium Catalysis. Issue 1 (25th November 2014)

• Record Type: Journal Article
• Authors: Feng, Ruokun; Wang, Binjie; Liu, Yue; Liu, Zhanxiang; Zhang, Yuhong
• Is Part Of: European journal of organic chemistry. Issue 1(2015)
• Page Start: 142
• Page End: 151
• Publication Date: 2014-11-25
• Subjects: Homogeneous catalysis -- Palladium -- C–H activation -- Amino acids -- Proline -- Directing groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403191
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A highly effective protocol for the synthesis of C‐3‐substituted prolines has been developed. Pd‐catalyzed C(sp 3 )–H activation is used for the straightforward functionalization of prolines. The use of an 8‐aminoquinolinecarboxamide directing group allows direct arylation, alkenylation, and alkylation at the C‐3 position of prolines in moderate to high yields with diverse iodo‐ or bromo precursors. The resulting 3‐substituted proline derivatives are important units in many biologically active compounds and are useful promoters for a variety of functional group transformations. Abstract : A highly effective protocol for the synthesis of C‐3‐substituted prolines has been developed. Pd‐catalyzed C(sp 3 )–H activation is used for the straightforward functionalization of prolines. The use of an 8‐aminoquinolinecarboxamide directing group allows direct arylation, alkenylation, and alkylation at the C‐3 position of prolines in moderate to high yields with diverse iodo‐ or bromo precursors.