Planar Chiral Arylaldehydeimine Tricarbonylchromium Complexes in the Asymmetric Baylis - Hillman Coupling Reaction

Aza‐Baylis–Hillman Reactions and Their Synthetic Applications

“…[33] In the presence also of DABCO as catalyst, the corresponding aza-BaylisHillman adducts were obtained in good yields. Removal of the metal provided chiral amines in high yields and enantiomeric excesses (Scheme 27).…”

“…In 1994, Kündig et al explored the reaction behavior of methyl acrylate and acrylonitrile in the presence of enantiopure planar chiral o-substituted Cr(CO) 3 . [33] In the presence also of DABCO as catalyst, the corresponding aza-Baylis-Hillman adducts were obtained in good yields. Removal of the metal provided chiral amines in high yields and enantiomeric excesses (Scheme 27).…”

Chiral Amines Derived from Asymmetric Aza‐Morita–Baylis–Hillman Reaction

“…Under the catalysis of DABCO, the corresponding aza-MBH adducts were obtained in good yields. Removal of the metal provided chiral amines in high yields and enantiomeric excesses [12]. Later on, Aggarwal et al used enantiopure N-sulfinimines in the aza-MBH reaction with methyl acrylate in the presence of 3-hydroxyquinuclidine (3-HQD) and Lewis acid.…”

New, Simple and Versatile Synthesis of Protected α-Alkylidene-β-amino Acids from Activated Vinylphosphonates

“…A Baylis-Hillman reaction was performed with acrylates or acrylonitrile as activated olefins and imines 2,10 or enantiomerically pure osubstituted benzaldehyde imine Cr(CO) 3 complexes. 11 Baylis-Hillman adducts were usually converted into allyl bromides 12 or acetates 13 and reacted with amines or further transformed into trichloroacetimidates 9,14 or carbamates 15 and treated with a base. Another, well documented approach to 1 is conjugate addition of R 2 CuLi 16,17 or DIBAL-H 3 to 2-alkynoates followed by nucleophilic addition of thus formed organometallic intermediates to imines.…”