REAGENTS FOR ASYMMETRIC ALLYLATION, ALDOL, AND TANDEM ALDOL AND ALLYLATION REACTIONS

摘要

A new class of reagents and method of use of the reagents in the reaction of the reagents with electrophilic compounds. The invention in one embodiment is directed to a method for the formation of an alcohol of the formula (I). The method includes reacting a reagent of the formula (II) with an aldehyde of the formula R10CHO to form the alcohol. X3 is one of O and C(R4)(R5). Each of X1 and X2 is independently O or N-R. Each of Ca and Cb is independently an achiral center, an (S) chiral center or an (R) chiral center. Ra and Rb are (i) each independently C1-10 alkyl, C6-10 aryl or C3-9 heteroaryl, or (ii) taken together to form a C3-C4 alkylene chain which together with Ca and Cb forms a 5-membered or 6-membered aliphatic ring. Rc and Rd are each independently hydrogen, C1-10 alkyl, C6-10 aryl or C3-9 heteroaryl. R is C1-10 alkyl, C6-10 aryl or C3-9 heteroaryl. Each of R1, R2, R3, R4, R5 is independently hydrogen, C1-C10 alkyl, C6-10 aryl, C3-9 heteroaryl, C1-10 alkoxy, C6-10 aryloxy, C1-10 dialkylamino, C1-10 alkyl-C6-10 arylamino, C1-10 diarylamino, or halogen. R6 is halogen, hydrogen, C1-10 alkyl, C6-10 aryl, C3-9 heteroaryl, C1-10 alkoxy, C6-10 aryloxy, C1-10 alkyl-C6-10 arylamino, C1-10 diarylamino, OSO2CF3 or SR. R10 may be C1-10 alkyl, C6-10 aryl, or C3-9 heteroaryl.