Addition of Terminal Acetylides to CO and CN Electrophiles

N‐Phosphinyl Imine Chemistry (I): Design and Synthesis of Novel N‐Phosphinyl Imines and their Application to Asymmetric aza‐Henry Reaction

“…Chiral phosphinamide (3) was prepared starting from phosphinic chloride (2), which required the synthesis of phosphinic acid (1). Phosphinic acid was synthesized using the known procedure (61).…”

“…Imine chemistry has been playing a crucial role for drug development and discovery because most drugs and their precursors contain amino functionality; this places imine chemistry among the most important and active research areas in modern organic, bioorganic, and medicinal chemistry (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). b-Nitroamines are particularly important synthetic precursors because of their easy conversion into many other useful building blocks, such as vicinal diamines and a-amino acids (13)(14)(15)(16)(17).…”

“…yields and 91% to >99% de the control of regio-, enantio-, and chemoselectivity for asymmetric reactions (4,7,(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38). Even though a great progress has been made in this field, the continuous search of new imines with superior properties for general use and for asymmetric synthesis still remains challenging (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12).…”

Zinc mediated direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones and mechanistic insight

“…3 The C-C triple bond adjacent to N -hydroxylamine facilitated its versatile modes of action (e.g. oxidative cleavage, 4 reduction, 5 hydrogenation, 6 hydroboration, and cyclization 7 ) to a wide number of synthetically useful building blocks including amino acids, isoxazolines, amines, keto-amines, and lactams.…”

Alkylzinc‐Mediated Addition of Alkynes to N‐Tosylaldimines: Enantioselective Synthesis of (E)‐(2‐En‐3‐ynyl)‐amines

“…[1] In this field, the addition of an acetylenic reagent to carbonyl compounds or imines is one of the most important objectives, and the resulting propargylic alcohols or amines are versatile building blocks for the preparation of natural products, pharmaceuticals and plant protective agents. [2] Some excellent on promotion of the reactions of acetylenes with imines in high yields and enantioselectivities are known. In this context, the most reliable and efficient method for the preparation of propargylic amines is the addition of an appropriate alkynyl-metal to achiral imines or imines bearing chiral auxiliaries.…”