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  • 09월 08일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Enantioselective Synthesis of ß-Aryl Amines via Direct Reductive Amination Catalyzed Chiral Phosphoric Acid

등록일
2015년 8월 27일 16시 18분 51초
접수번호
0993
발표코드
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발표시간
목 09시 : 00분
발표형식
구두발표
발표분야
유기화학 - Oral Presentation of Graduate Scholars in Organic Division
저자 및
공동저자
김경희, 천철홍*
고려대학교 화학과, Korea

Over the past decade, chiral phosphoric acid catalysis has become one of the most rapidly growing fields in asymmetric catalysis. Among the various asymmetric reactions that involve a chiral phosphoric acid catalyst, asymmetric reduction of ketimines with organic hydride sources has become one of the most popular reactions in enantioselective phosphoric acid catalysis. Although a number of examples of the synthesis of chiral amines through chiral phosphoric acid-catalyzed asymmetric reduction of ketimines have been reported, most of the previous examples have been limited to the synthesis of chiral α-aryl amines via enantioselective reduction of ketimines derived from alkyl aryl ketones. Thus, we have developed a new method for the synthesis of chiral ß-aryl amines via chiral phosphoric acid-catalyzed asymmetric reductive amination of benzyl methyl ketones using Hantzsch ester as an organic hydride source. A variety of benzyl methyl ketone derivatives bearing various aryl groups were applicable to this protocol to afford the desired chiral ß-aryl amines in high yields and good enantioselectivity. Furthermore, the resulting chiral β-aryl amine was successfully transformed to tetrahydroisoquinoline, which is one of the key building blocks in a series of naphthylisoquinoline alkaloids. Moreover, we further attempted to apply this protocol to the synthesis of a naphthylisoquinoline moiety found in natural product.


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