Very recently, we[1] found that L-proline amides and dipeptides acted as efficient catalysts for the asymmetric direct aldol reaction. We report here that L-proline-based peptides 1~5 can catalyze the aldol reactions ...Very recently, we[1] found that L-proline amides and dipeptides acted as efficient catalysts for the asymmetric direct aldol reaction. We report here that L-proline-based peptides 1~5 can catalyze the aldol reactions of hydroxyacetone with aldehydes 6 in aqueous media, to give 1,4-diols (7), the disfavored products with either aldolase or L-proline. Both peptides 3 and 4 give good results.……展开更多
As our continuous efforts to search for easily accessible ligands for dialkylzinc addition to imines,[1] in this paper,we would like to present a family of chiral imino alcohols 3 derived from 1,2-diphenyl-2-aminoetha...As our continuous efforts to search for easily accessible ligands for dialkylzinc addition to imines,[1] in this paper,we would like to present a family of chiral imino alcohols 3 derived from 1,2-diphenyl-2-aminoethanol which will be evaluated for the titled reaction. We believed that this kind of chiral ligands could be good chiral ligands for the diethylzinc addition to imines based on two points: (1) The excellent asymmetrically inductive properties of 1,2-diphenyl-2-aminoethanol and its derivatives have been proven in many reactions. (2) The conformation of the nitrogen in the chiral imines 3 is restricted by imine function which is similar to chiral oxazolines reported in our recent work.……展开更多
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
文摘Very recently, we[1] found that L-proline amides and dipeptides acted as efficient catalysts for the asymmetric direct aldol reaction. We report here that L-proline-based peptides 1~5 can catalyze the aldol reactions of hydroxyacetone with aldehydes 6 in aqueous media, to give 1,4-diols (7), the disfavored products with either aldolase or L-proline. Both peptides 3 and 4 give good results.……
文摘As our continuous efforts to search for easily accessible ligands for dialkylzinc addition to imines,[1] in this paper,we would like to present a family of chiral imino alcohols 3 derived from 1,2-diphenyl-2-aminoethanol which will be evaluated for the titled reaction. We believed that this kind of chiral ligands could be good chiral ligands for the diethylzinc addition to imines based on two points: (1) The excellent asymmetrically inductive properties of 1,2-diphenyl-2-aminoethanol and its derivatives have been proven in many reactions. (2) The conformation of the nitrogen in the chiral imines 3 is restricted by imine function which is similar to chiral oxazolines reported in our recent work.……
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).……