91564-35-1Relevant academic research and scientific papers
Asymmetric Syntheses of (-)-ADMJ and (+)-ADANJ: 2-Deoxy-2-amino Analogues of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin
Davies, Stephen G.,Figuccia, Aude L. A.,Fletcher Paul, Ai M.,Roberts,Thomson, James E.
, p. 6481 - 6495 (2016/08/16)
The asymmetric syntheses of (-)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-opening of the corresponding aziridinium intermediates with a tethered carbamate moiety) to give oxazolidin-2-ones was initially optimized on a model system. Subsequent application of this methodology to two enantiopure bishomoallylic amines (which were produced via aminohydroxylation of an α,β-unsaturated ester, partial reduction, and reaction of the corresponding aldehyde with vinylmagnesium bromide) also proceeded with concomitant N-debenzylation to afford the corresponding diastereoisomerically pure (>99:1 dr) oxazolidin-2-ones. Subsequent deprotection of these enantiopure templates gave (-)-ADMJ and (+)-ADANJ as single diastereoisomers in 16% and 24% overall yield, respectively.
Synthetic approaches to a chiral 4-amino-3-hydroxy piperidine with pharmaceutical relevance
Ortiz, Adrian,Young, Ian S.,Sawyer, James R.,Hsiao, Yi,Singh, Amarjit,Sugiyama, Masano,Corbett, R. Michael,Chau, Melissa,Shi, Zhongping,Conlon, David A.
supporting information; experimental part, p. 5253 - 5257 (2012/08/08)
Four synthetic strategies were evaluated towards the preparation of (-)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol (1), which was constructed with control over the relative and absolute stereochemistry of the 4,3-amino alcohol moiety. The first strategy employed a novel RhI catalyzed asymmetric hydrogenation, while two other strategies exploited the existing stereochemistry in 2-deoxy-d-ribose, and the fourth explored both biocatalytic and classical resolution techniques as a means to impart enantioenrichment to racemic intermediates en route to targeted structure (-)-1. The Royal Society of Chemistry 2012.
