101708-85-4Relevant academic research and scientific papers
Regio- and stereo-controlled addition reaction of aminoallylic stannanes to aldehydes mediated by germanium dichloride
Suzuki, Kensuke,Nishimoto, Yoshihiro,Yunoki, Hiroshi,Tsuruwa, Kensuke,Esumi, Naoto,Yasuda, Makoto
, p. 821 - 824 (2018)
A GeCl2-mediated addition reaction of α-(N-phthaloylamino) allylic stannane to aldehydes was achieved to give 1, 2-amino alcohol derivatives in high anti-selectivity. Various types of aromatic and aliphatic aldehydes were applicable. The synthesized N-phthaloylamino alcohols were smoothly transformed to aminoalcohols by conventional methods with no loss of stereochemistry.
Chemistry of N-Boc-N-tert-butylthiomethyl-protected alpha-aminoorganostannanes: diastereoselective synthesis of primary beta-amino alcohols from alpha-aminoorganostannanes.
Ncube, Adela,Park, Sheldon B,Chong, J Michael
, p. 3625 - 3636 (2007/10/03)
Reaction of N-Boc-N-tert-butylthiomethyl-protected alpha-aminoorganostannanes with n-BuLi generates the corresponding alpha-aminoorganolithiums. Reactions of these organolithiums with aromatic aldehydes provides N-protected beta-amino alcohols with diastereoselectivities up to >99:1 anti/syn; with aliphatic aldehydes, diastereoselectivities were typically 1:1. Diastereoselectivities varied depending on the amount of aldehyde used. The N-protected beta-amino alcohols could be deprotected to primary amines by treatment with NaH to generate oxazolidinones followed by basic hydrolysis. Alternatively, treatment of the protected amino alcohols with acid furnished cyclic acetals that could be deprotected to primary amines with BF(3).OEt(2) and HS(CH(2))(3)SH. Transmetalation of enantiomerically enriched organostannanes with n-BuLi at -95 degrees C provided organolithiums that, although less configurationally stable than N-Boc-N-methyl-protected alpha-aminoorganolithiums, could be trapped with aldehydes with near-complete retention of configuration.
