551000-83-0Relevant articles and documents
Scalable Asymmetric Synthesis of the All Cis Triamino Cyclohexane Core of BMS-813160
Deerberg, Joerg,Eastgate, Martin D.,Fan, Yu,Galella, Michael A.,Galindo, Kay A.,González-Bobes, Francisco,Kopp, Nathaniel,La Cruz, Thomas E.,Pathirana, Charles,Sfouggatakis, Chris,Xiao, Yi,Zheng, Bin
, (2021/09/02)
BMS-813160 is a pharmaceutical entity currently in development at Bristol Myers Squibb. Its defining structural feature is a unique chiral all cis triamino cyclohexane core. Medicinal and process chemistry groups at BMS have previously published synthesis
α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights
Calvet, Géraldine,Coote, Susannah C.,Blanchard, Nicolas,Kouklovsky, Cyrille
experimental part, p. 2969 - 2980 (2010/06/20)
α-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a β-oxygenated moiety led to a domino [4+2] cycloaddition/σN-O bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the σN-O bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported.
Efficient cleavage of the N-O bond of 3,6-dihydro-1,2-oxazines mediated by some α-hetero substituted carbonyl compounds in mild conditions
Galvani, Gilles,Calvet, Geraldine,Blanchard, Nicolas,Kouklovsky, Cyrille
scheme or table, p. 1063 - 1070 (2009/02/05)
The efficient cleavage of the N-O bond of some nitroso Diels-Alder cycloadducts has been achieved in mild conditions, mediated either by 2,2-dimethyl-1,3-dioxan-5-one or 1,3-dithiolane-2-carboxaldehyde. These new and purely organic conditions allow an exc