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  • 09월 01일 18시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제118회 대한화학회 학술발표회, 총회 및 기기전시회 안내 L-Proline catalyzed enantioselective synthesis of β-carbonyl amino acid derivatives via anti-Mannich reaction of cyclicimines with ketones

2016년 9월 1일 13시 43분 03초
ORGN.P-429 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 14일 (금요일) 11:00~12:30
저자 및
김동환, 이희순1, 정재경1,*
충북대학교 약학대학, Korea
1충북대학교 제약학과, Korea
β-carbonyl amino acid derivatives represent an important structural unit have always fascinated by organic chemists because of its ubiquitous in nature, found in many natural and bioactive compounds. Over the years, number of approaches have been developed, among them Mannich reactions are very well known method. Considerable efforts have been devoted toward the development of syn-Mannich reaction. On the other hand, there are only few reports are available for the synthesis of anti-Mannich product, though most of the approaches were using β-proline and other and costly catalysts. Thus far, the development of efficient approach for anti-Mannich reaction by using economically cheap catalyst is in high demand. In this study, we have developed highly enantioselective anti-Mannich reaction of various cyclicimines with ketones by using simple L-proline (30 mol%) as catalyst. When unsymmetrical ketone used as Mannich donor, we have obtained linear product as major over the branch. The protecting group can be easily removed and furnished α-amino acid derivatives. By using our optimized condition, wide range of β-carbonyl amino acid derivatives were directly obtained in shorter reaction time in anti-conformation with excellent enantiomeric excess (up to 99% ee) and diastereoselectivities (dr ratio, up to 10:1).