Homoallylamines from aldimines and allylstannanes

Abstract

The first examples of the carbonylation of mercaptans are described: cobalt carbonyl catalyzes the desulfurization and carbonylation of mercaptans to carboxylic esters by means of carbon monoxide in aqueous alcohol.Sir: Carbonylation reactions are an important class of organic reactions. Of industrial importance are those transformations utilizing olefins, alkynes, and halides as For example, benzylic halides as well as vinylic monoor dibromides can be carbonylated to acids by cobalt carbonyl (eq 1)3 or palladi~m (0)~ catalysts under (1) Wender, I., Pino, P., Eds. "Organic Synthesis via Metal Carbonyls"; (2) Falbe, J., Ed. "New Syntheses with Carbon Monoxide"; Springer (3) Alper, H.; des Abbayes, H.

Stereoselective synthesis of three-membered ring compounds via ylide routes

“…Encouraged by the successful activation of imines by Lewis acids in allylation reactions [19] and aziridination [20] of BF 3 ؒ OEt 2 activated imines with ethyl diazoacetate, we examined the BF 3 ؒ , OEt 2 and TMSCl activation of imines in the ylide reaction for the preparation of vinyl-and ethynylaziridines (eqn 10, Scheme 9). A variety of aromatic aldimines, either N-aryl or N-alkyl, could be aziridinated with good to excellent yields, but aziridination failed when aliphatic aldimines were used as substrates.…”

Synthesis of homoallylic amines and acylhydrazides by tin powder‐promoted multicomponent one‐pot allylation reactions

“…[9][10][11][12][13][14][15][16][17][18][19][20][21] As reported in the literature, allylic organometallics such as allylic Mg, [22,23] Zn, [24,25] In, [26][27][28][29] Sn, [30][31][32][33][34][35][36][37][38] Si, [39,40] B [25,41] and Sm [42,43] have been intensively investigated in allylation reactions. Among these organometallics, allylic stannanes have been widely used because of their easy availability, air and moisture stability, tolerance to functional groups and high selectivity.…”

Zirconyl Chloride (= Dichlorooxozirconium) as an Efficient Catalyst for One‐Pot Multicomponent Synthesis of Homoallylic Amines

“…-Homoallylic amines are useful intermediates for the synthesis of various bioactive natural products and related compounds [1]. They are generally prepared by allylation of imines with allyl organometallics in the presence of a catalyst such as BF 3 [3]. The one-pot method involving the in situ generation of imines from aldehydes and amines followed by allylation is more convenient for the synthesis of these compounds [4].…”