189438-85-5Relevant articles and documents
Palladium-catalyzed allylation of imines with allyl alcohols
Shimizu, Masamichi,Kimura, Masanari,Watanabe, Toshiya,Tamaru, Yoshinao
, p. 637 - 640 (2007/10/03)
(Chemical Equation Presented) A catalytic system, Pd(OAc)2 (10 mol %)-P(n-Bu)3 (20 mol %)-Et3B (360 mol %), promotes allylic alcohols to undergo the allylation of anisidineimines of aromatic and aliphatic aldehydes and furnishes homoallylamines in good to moderate yields. The reaction shows unique stereoselectivity, giving anti-isomers selectively.
Highly diastereoselective and enantioselective preparation of homoallylic amines: Application for the synthesis of β-amino acids and γ-lactams
Ramachandran, P. Veeraraghavan,Burghardt, Thomas E.
, p. 4387 - 4395 (2007/10/03)
Reactions of N-silyl- and N-aluminoimines with B- allyldiisopinocampheylborane in the presence of methanol, followed by oxidative workup furnished homoallylic amines in good yields and high ee. A 11B NMR spectroscopy study revealed that the reactions do not proceed, even at room temperature, unless a molar equivalent of water or methanol is added. The first reagent-controlled asymmetric crotylboration and alkoxyallylboration of aldimines furnishing β-methyl or βalkoxy homoallylic amines in very high diastereoselectivity and enantioselectivity are reported herein. Crotylboration and alkoxyallylboration of imines proceed only with the "allyl"-boron "ate" complexes, instead of the "allyl"-dialkylboron reagents used with aldehydes. The addition of methanol is necessary for these reactions as well. Application of this methodology for the conversion of representative nitriles to β-amino acids in two steps has been described. Additionally, a procedure for the preparation of chiral δ-amino alcohols and γ-lactams from nitriles is also reported.
Organometallic reactions in aqueous media. Indium-mediated allylation of sulfonimines
Chan, Tak Hang,Lu, Wenshuo
, p. 8605 - 8608 (2007/10/03)
Barbier-type allylation of sulfonimines with indium and allyl bromide to give homoallylic sulfonamides can be performed smoothly in organic solvents and in aqueous media. The regio- and the stereoselectivity of the reaction have been examined.