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 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 C_a and C_b is independently an achiral center, an (S) chiral center or an (R) chiral center. R_a and R_b are (i) each independently C_1-10 alkyl, C_6-10 aryl or C_3-9 heteroaryl, or (ii) taken together to form a C₃-C₄ alkylene chain which together with C_a and C_b forms a 5-membered or 6-membered aliphatic ring. R_c and R_d are each independently hydrogen, C_1-10 alkyl, C_6-10 aryl or C_3-9 heteroaryl. R is C_1-10 alkyl, C_6-10 aryl or C_3-9 heteroaryl. Each of R¹, R², R³, R⁴, R⁵ is independently hydrogen, C₁-C₁₀ alkyl, C_6-10 aryl, C_3-9 heteroaryl, C_1-10 alkoxy, C_6-10 aryloxy, C_1-10 dialkylamino, C_1-10 alkyl-C_6-10 arylamino, C_1-10 diarylamino, or halogen. R⁶ is halogen, hydrogen, C_1-10 alkyl, C_6-10 aryl, C_3-9 heteroaryl, C_1-10 alkoxy, C_6-10 aryloxy, C_1-10 alkyl-C_6-10 arylamino, C_1-10 diarylamino, OSO₂CF₃ or SR. R¹⁰ may be C_1-10 alkyl, C_6-10 aryl, or C_3-9 heteroaryl.