As a versatile chiral ammonia equivalent, chiral tert-butylsulfinylamide (6) (TBSA) is a very useful auxiliary due to the characteristics of highly stereoselectivity in asymmetric induction and the sulfinyl group bein...As a versatile chiral ammonia equivalent, chiral tert-butylsulfinylamide (6) (TBSA) is a very useful auxiliary due to the characteristics of highly stereoselectivity in asymmetric induction and the sulfinyl group being easily removed compared with other amine auxiliaries since its introduction as a stable compound by Ellman in 1997.[1] Considering the importance of TBSA 6, search for efficient methods for the preparation of enantiopure TBSA (6) is the great interesting topic in synthetic chemistry. There were only three methods for the preparation of enantiopure TBSA (6) reported in the literature.[2] In this paper, we report an alternative three-step procedure to synthesize enantiopure TBSA (6) with a key step being the formation of tert-butylsulfinyloxazolidinone (4).……展开更多
基金Project supported by the National Natural Science Foundation of China (No. 20372048) and the Ministry of Education (EYTP).
文摘As a versatile chiral ammonia equivalent, chiral tert-butylsulfinylamide (6) (TBSA) is a very useful auxiliary due to the characteristics of highly stereoselectivity in asymmetric induction and the sulfinyl group being easily removed compared with other amine auxiliaries since its introduction as a stable compound by Ellman in 1997.[1] Considering the importance of TBSA 6, search for efficient methods for the preparation of enantiopure TBSA (6) is the great interesting topic in synthetic chemistry. There were only three methods for the preparation of enantiopure TBSA (6) reported in the literature.[2] In this paper, we report an alternative three-step procedure to synthesize enantiopure TBSA (6) with a key step being the formation of tert-butylsulfinyloxazolidinone (4).……
