57475-39-5Relevant academic research and scientific papers
The threo-Selective Reaction of Allenic Organometallic Compounds with Imines
Yamamoto, Yoshinori,Ito, Wataru,Maruyama, Kazuhiro
, p. 1004 - 1005 (1984)
The reaction between the imines (2) and the allenic organometallic compounds (3) gives the threo adducts (4) with very high stereoselectivity, while the reaction with 9-but-2-enyl-9-borabicyclononane gives the analogous erythro allylamines stereoselectively.
Allylation of aldimines promoted by NbCl5
Andrade, Carlos Kleber Z,Oliveira, Guilherme R
, p. 1935 - 1937 (2007/10/03)
Niobium chloride promoted the addition of allylstannanes to aromatic aldimines. Excellent syn diastereoselectivity was obtained in the addition of crotylstannane to N-benzylideneaniline (46:1).
NbCl5: A novel Lewis acid in allylation reactions
Andrade, Carlos Kleber Z.,Azevedo, Neucírio R.,Oliveira, Guilherme R.
, p. 928 - 936 (2007/10/03)
Allylation reactions promoted by niobium pentachloride are described. Allylstannanes were added to aromatic and aliphatic aldehydes and aromatic imines in good yields. Excellent syn diastereoselectivities were obtained in the addition of (E)-cinnamylstannane to benzaldehyde (49:1) and in the addition of crotylstannane to N-benzylideneaniline (46:1).
Synthesis of Homoallylamines by the Addition of Allylic Indium Reagents to Azomethines and Nitriles
Jin, Shun-Ji,Araki, Shuki,Butsugan, Yasuo
, p. 1528 - 1532 (2007/10/02)
Triallyldiindium trihalides and allylindate(1-)s reacted with N-benzylideneamines regioselectively at the C-3 carbon on the allyl group to give high yields of homoallylic secondary amines.Primary amines were obtained by the action of an excess of allylic
Diastereofacial Selectivity in the Reaction of Allylic Organometallic Compounds with Imines. Stereoelectronic Effect of Imine Group
Yamamoto, Yoshinori,Komatsu, Toshiaki,Maruyama, Kazuhiro
, p. 3115 - 3121 (2007/10/02)
The diastereofacial selectivity in the reaction of crotyl organometallic compounds (4) (M = Li+, Mg, B, and Sn) with imines (3) is investigated.The reaction of ordinary imines produces the erythro isomer (5) predominantly regardless of the metal (M).With increase of the steric bulk of the R group or with aryl substituent in the R' group, the threo isomer (6) predominates in the reaction of crotyl-9-BBN.The ratio of erythro (11)/threo (12) in the reaction of pent-3-en-2-yl-9-BBN (9) is higher then the ratio of erythro (5)/threo (6) in the reaction of crotyl-9-BBN itself.On the basis of these observations, the transition-state geometry is discussed.
