Patent Number: 7,534,905

Title: Reagents for asymmetric allylation, aldol, and tandem aldol and allyation reactions

Abstract: 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 R.sup.10CHO to form the alcohol. X.sub.3 is one of O and C(R.sup.4)(R.sup.5). Each of X.sub.1 and X.sub.2 is independently O or N--R. Each of C.sub.a and C.sub.b is independently an achiral center, an (S) chiral center or an (R) chiral center. R.sub.a and R.sub.b are (i) each independently C.sub.1-10 alkyl, C.sub.6-10 aryl or C.sub.3-9 heteroaryl, or (ii) taken together to form a C.sub.3--C.sub.4 alkylene chain which together with C.sub.a and C.sub.b forms a 5-membered or 6-membered aliphatic ring. R.sub.c and R.sub.d are each independently hydrogen, C.sub.1-10 alkyl, C.sub.6-10 aryl or C.sub.3-9 heteroaryl. R is C.sub.1-10 alkyl, C.sub.6-10 aryl or C.sub.3-9 heteroaryl. Each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 is independently hydrogen, C.sub.1--C.sub.10 alkyl, C.sub.6-10 aryl, C.sub.3-9 heteroaryl, C.sub.1-10 alkoxy, C.sub.6-10 aryloxy, C.sub.1-10 dialkylamino, C.sub.1-10 alkyl-C.sub.6-10 arylamino, C.sub.1-10 diarylamino, or halogen. R.sup.6 is halogen, hydrogen, C.sub.1-10 alkyl, C.sub.6-10 aryl, C.sub.3-9 heteroaryl, C.sub.1-10 alkoxy, C.sub.6-10 aryloxy, C.sub.1-10 alkyl-C.sub.6-10 arylamino, C.sub.1-10 diarylamino, OSO.sub.2CF.sub.3 or SR. R.sup.10 may be C.sub.1-10 alkyl, C.sub.6-10 aryl, or C.sub.3-9 heteroaryl. ##STR00001##

Inventors: Leighton; James L. (New York, NY), Wang; Xiaolun (New York, NY), Kinnaird; James (Kent, GB)

Assignee: The Trustees of Columbia University In the City of New York

International Classification: C07F 7/10 (20060101); C07F 7/08 (20060101); C07F 7/18 (20060101)

Expiration Date: 2021-05-19 0:00:00