【摘 要】
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Pudovik reaction,1 the addition of P-H compounds to aldehydes and imines,is one of the most general,straightforward,and widely-applied method for the construction of P-C bonds.Due to the biological ac
【机 构】
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College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035;National Institut
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Pudovik reaction,1 the addition of P-H compounds to aldehydes and imines,is one of the most general,straightforward,and widely-applied method for the construction of P-C bonds.Due to the biological activities and pharmaceutical applications of the α-aminoacid like products and related derivatives,numerous reports and reviews have focused on the reaction,including asymmetric synthesis of α-hydoxy and α-amino phosphorus compounds.In contrast,examples of substrate-controlled diastereoselective Pudovik reaction were limited and not successful.2 In the course of our study,3 we found optically pure (-)-menthyl (RP)-phenyl phosphinate 1a readily reacts with aldehydes to produce high yields of optically active α-hydoxyphosphinates 2 with high dr (up to 97/3),creating a new chiral carbon center via a substrate-controlled highly diastereoselective Pudovik reaction.Epimerization of substrate 1a to 1b,which leads to the formation of byproduct 3 with inversed configuration at phosphorus,can be avoided (2/3 up to 100/0) by using simple achiral rhodium or iridium complexes as the catalysts.X-ray analysis showed that an (R)-configuration at the new chiral carbon centre (the hydroxyl carbon) was generated,as well as that the absolute configuration at the phosphorus was retained during the addition.
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