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

제116회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Asymmetric Synthesis of Chiral Pyrrolopiperazine Derivatives via Diaza-Cope Rearrangement

등록일
2015년 9월 8일 13시 33분 26초
접수번호
1374
발표코드
ORGN.P-456 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
송명종, 김병문*
서울대학교 화학부, Korea

An efficient synthetic method was developed for the construction of enantiomerically pure pyrrolopiperazine derivatives using diaza-Cope rearrangement (DCR) as a key step starting from (R,R)/(S,S)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (HPEN). A complete transfer of stereochemical integrity was observed for the transformation. Pyrrolopiperazine is a useful building block often employed in the design of biological active molecules.1 This functionality is found in nootropic drugs like unifiram that is used as memory enhancers.2 Additionally, these types of chiral diamines were used as chiral ligands in the reduction of prochiral ketones by treatment of a mixture of stannous chloride and a diamine with diisobutylaluminium hydride.3 We previously showed that diaza-Cope rearrangement reactions can be used to make a wide variety of alkyl- and aryl-substituted diamines as well as non-symmetrically substituted diamines.4 Herein, we report stereospecific synthesis of chiral pyrrolopiperazine derivatives by using the rearrangement reaction.


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