SIMPLE ORGANIC MOLECULES AS CATALYSTS FOR PRACTICAL AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF AMINES AND ALCOHOLS

摘要

The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules.

主权项

1. A compound of formula I: wherein: n is 0-10; each R1 is independently R, halogen, —OR, —N(R)2, —SR, —NO2, —SOR, —SO2R, —Si(R)3, or —C(O)L; X is —O—, —NR—, —S—, or —Se—; X′ is —O—, —NR6—, —S—, or —Se—; Z is —C(R2)2—NR—, —C(R2)═N—, or —C(═Y)—NR—; Y is ═O, ═S, or ═NR; each of R2, R3, R4, R5 and R6 is independently R, —OR, —N(R)2, —SR, or —C(O)L; L is R, halogen, —OR, —N(R)2, or —SR; each R is independently hydrogen or R′; and each R′ is independently an optionally substituted group selected from C1-12 aliphatic, phenyl, a 3-7 membered saturated or partially unsaturated carbocyclic ring, an 8-10 membered bicyclic saturated, partially unsaturated or aryl ring, a 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 4-7 membered saturated or partially unsaturated heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 7-10 membered bicyclic saturated or partially unsaturated heterocyclic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered bicyclic heteroaryl ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or
two R′ groups on the same nitrogen atom are optionally taken together with the nitrogen atom to form an optionally substituted 3-8 membered, saturated, partially unsaturated, or aryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; ortwo R′ groups on the same carbon atom are optionally taken together with their intervening atoms to form an optionally substituted 3-8 membered saturated or partially unsaturated spirocycle ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; ortwo R′ groups on adjacent atoms are optionally taken together with their intervening atoms form an optionally substituted 3-8 membered, saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.