93965-53-8Relevant academic research and scientific papers
One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine
Itabashi, Suguru,Shimomura, Masashi,Sato, Manabu,Azuma, Hiroki,Okano, Kentaro,Sakata, Juri,Tokuyama, Hidetoshi
, p. 1786 - 1790 (2018/07/03)
A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.
Preparation and reactions of masked allylic organozinc reagents
Jones, Philip,Knochel, Paul
, p. 186 - 195 (2007/10/03)
Allylic zinc reagents have been prepared from sterically hindered homoallylic alcohols 10 and 13, using a novel fragmentation reaction of the corresponding zinc alkoxide, without any homocoupling products. These allylic zinc reagents react with a range of electrophiles in good to excellent yields. Substituted allylic zinc reagents have also been prepared in this manner. α-Substituted homoallylic alcohols 37, 46, and 51 give solely α- substituted products after the fragmentation-allylation sequence; these products are obtained not only regioselectively but also with extremely high anti diastereoselectivity. Likewise, γ-substituted homoallylic alcohols 57 and 58, undergo the fragmentation-allylation reaction to give γ-substituted products. The reaction has also been demonstrated to be catalytic in zinc salts.
Masked allylic zinc reagents
Jones, Philip,Millot, Nicolas,Knochel, Paul
, p. 2405 - 2406 (2007/10/03)
The preparation of allylic zinc reagents using the fragmentation of sterically hindered tertiary homoallylic alcohols is described.
A NOVEL "Ti(0)" INDUCED ALLYLATION OF AMINES IN A TiCl4 (cat.)/ Al BIMETAL SYSTEM. CHIRALITY TRANSFER OF l-VALINE TO HOMOALLYLAMINE
Tanaka, Hideo,Inoue, Keizo,Pokorski, Ulrike,Taniguchi, Masatoshi,Torii, Sigeru
, p. 3023 - 3026 (2007/10/02)
"Barbier Type" allylation of imines with allyl bromide has been performed successfully by the action of aluminium (1 equiv.) and titanium(IV) chloride (0.05 equiv.) in THF.The chirality transfer of α-amino acid esters to homoallyl amines is demonstrated b
ELECTROREDUCTIVE "BARBIER TYPE" ALLYLATION OF IMINES WITH A COMBINATION OF A Pb(O)/Pb(II) REDOX MEDIATOR AND SACRIFICAL ANODE (Al)
Tanaka, Hideo,Nakahara, Takao,Dhimane, Hamid,Torii, Sigeru
, p. 4161 - 4164 (2007/10/02)
An electroreductive "Barbier Type" allylation of imines with allyl bromide has been performed in a PbBr2/Bu4NBr/THF-(Al anode)-(Pt cathode) system.A combination of Pb(O)/Pb(II) redox and a sacrifical aluminum anode works as a madiator for both cathodic an
Allylation of Imines with in situ Generated Allyl Lead Reagents in a PbBr2/Al/BF3*OEt2/Et2O System
Tanaka, Hideo,Yamashita, Shiro,Ikemoto, Youichi,Torii, Sigeru
, p. 673 - 674 (2007/10/02)
Reductive addition of allyl bromide to imines has been performed with a combination of a catalytic amount of PbBr2 (0.03-0.1 equiv.) and Al (1 equiv.) in Et2O containing BF3*OEt2 (1.1 equiv.).
Homoallylamines from Aldimines and Allylstannanes
Keck, Gary E.,Enholm, Eric J.
, p. 146 - 147 (2007/10/02)
Allyltri-n-butylstannane adds to aldimines in the presence of Lewis acids to give homoallylamines; for the analogous additions of crotyltri-n-butylstannane, bond construction selectivity is a sensitive function of the thermal history of the aldimine-Lewis
