Enantioselective phosphoramidite compounds and catalysts

Abstract

This invention relates to phosphoramidite compounds and catalyst complexes which can be used to provide enantioselective reactions including hydroamination reactions, etherification reactions and conjugate addition reactions and allylic substitution reactions, among others. In a first aspect, the present invention is directed to phosphoramidite and related compounds according to general structure (I), where Z is absent or is a group containing O, N or S, preferably O; R<1> and R<2> are independently an optionally substituted C1-12 alkyl group, an optionally substituted (CH2)n-aromatic group or (CH2)n-heteroaromatic group, or are linked together to form an optionally substituted aliphatic or (CH2)n-aromatic dianion of a diol, diamine, dithiol, aminoalcohol, aminohiolate or a alcoholthiol group; R<3'> and R<3> are each independently H, an optionally substituted C1-C12 alkyl group or an optionally substituted (CH2)n-aromatic group with the proviso that R<3'> and R<3> are not both H, or together R<3'> and R<3> form an optionally substituted C5-C15 saturated or unsaturated carbocyclic ring; R<4> is H, an optionally substituted C1-C12 alkyl group or an optionally substituted (CH2)n-aromatic group; R<5> is absent, H, an optionally substituted C1-C12 alkyl group or an optionally substituted (CH2)n-aromatic or (CH2)n-heteroaromatic group; R and R are each independently H or a C1-C3 alkyl group, or R and R together with the carbon to which they are attached form a optionally substituted C5-C15 saturated or unsaturated carbocyclic or heterocyclic ring, or an aromatic or heteroaromatic ring; R<6> and R<7> are each independently H, an optionally substituted C1-C12 alkyl group or an optionally substituted (CH2)n-aromatic group, with the proviso that R<5>, R<6> and R<7> cannot simultaneously be H, and when R and R, together with the carbon to which they are attached, form a carbocyclic ring.

Description

field of invention [0001] The present invention relates to phosphoramidite compounds and catalyst complexes useful for providing enantioselective reactions including hydroamination, etherification, and conjugate addition reactions, as well as allyl substitution reactions and the like. [0002] related application [0003] This application claims the benefit of priority from US Provisional Application US 60 / 566,969, filed April 29, 2004, which is hereby incorporated by reference in its entirety. [0004] governmental support [0005] This invention was made in part with Government support from the Naional Institutes of Health of the United States Department of Health and Human Services, Grant No. GM-55382. Accordingly, the United States Government has certain rights in this invention. Background of the invention [0006] Transition metal-catalyzed allyl substitution is an effective means of controlling carbon-carbon and carbon-heteroatom bond formation (Godleski, S.A.; Tro...

AI Technical Summary

Problems solved by technology

The relative importance of different stereochemical elements and the basis for differences in activity between catalysts formed from different diastereomeric ligands, in previous studies of enantioselective iridium-catalyzed processes or even in the determination of cyclometalated species The structure of the

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