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

Title:

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

Document Type and Number:

WIPO Patent Application WO2003074534

Kind Code:

A9

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<10>CHO to form the alcohol. X3 is one of O and C(R<4>)(R<5>). 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 R<1>, R<2>, R<3>, R<4>, R<5> 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. R<6> 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. R<10> may be C1-10 alkyl, C6-10 aryl, or C3-9 heteroaryl.

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Inventors:

LEIGHTON JAMES L (US)
KINNAIRD JAMES (GB)
WANG XIAOLUN (US)

Application Number:

PCT/US2003/006308

Publication Date:

November 20, 2003

Filing Date:

March 03, 2003

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Assignee:

UNIV COLUMBIA (US)
LEIGHTON JAMES L (US)
KINNAIRD JAMES (GB)
WANG XIAOLUN (US)

International Classes:

C07C33/14; C07C29/38; C07C33/20; C07C41/30; C07C41/56; C07C43/178; C07C43/23; C07C241/02; C07C241/04; C07C243/32; C07F7/02; C07F7/04; C07F7/08; C07F7/10; C07F7/12; C07F7/18; C07C243/28; (IPC1-7): C07F7/04

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