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제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Enantioselective Strecker reaction of Aldimines Activated by Chiral Oxazaborolidinium Ion with Trimethylsilyl Cyanide

2019년 2월 14일 14시 35분 12초
ORGN.P-338 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 18일 (목요일) 11:00~12:30
Organic Chemistry
저자 및
Sang Hyun Park, Do Hyun Ryu*
Department of Chemistry, Sungkyunkwan University, Korea
Enantioselective Strecker reaction is useful method in synthesizing chiral α-aminonitriles which are important building blocks for many natural products1. Various studies of nucleophilic addition to aldehydes or ketones in presence of chiral oxazaborolidinium ion(COBI) as Lewis acid catalyst have been previously reported by our group2. In this research, various aldimine compounds are catalyzed by chiral oxazaborolidinium ion for the enantioselective Strecker reaction. Three-component asymmetric process studied here significantly improves upon the original Strecker reaction to obtain excellent yield (up to 98%) and high enantioselectivity (up to 95%). References 1. Miyagawa S.; Yoshimura K.; Yamazaki Y.; Takamatsu N.; Kuraishi T.; Aiba S.; Tokunaga Y.; Kawasaki T. Angew. Chem. Int. Ed. 2017, 56, 1055-1058. 2. for selected reviews of enantioselective nucleophilic addition to aldehydes and ketones using COBI, see: (a) Kang, B. C.; Nam, D. G.; Ryu, D. H. Org. Lett. 2015, 17, 4810. (b) Kang, B. C.; Shin, S. H.; Yun, J.; Ryu, D. H. Org. Lett. 2017, 19, 6316.