144492-44-4

Upstream product

• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 100-46-9 benzylamine 

Downstream Products

• 186410-32-2 (S)-4-[(Benzyl-ethoxycarbonyl-amino)-phenylselanyl-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 234755-01-2 tert-butyl (4R,1S)-(1-benzylamino-3-trimethylsilylprop-2-ynyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 144541-27-5 cis-(3R,4S)-1-benzyl-3-<(R)-2-oxo-4-phenyloxazolidin-3-yl>-4-<(R)-3-<(tert-butoxycarbonyl)amino>-2,2-dimethyloxazolidin-4-yl>azetidin-2-one 
• 144541-26-4 cis-(3S,4R)-1-benzyl-3-<(R)-2-oxo-4-phenyloxazolidin-3-yl>-4-<(R)-3-<(tert-butoxycarbonyl)amino>-2,2-dimethyloxazolidin-4-yl>azetidin-2-one 
• 316821-35-9 (R)-3-[(2S,3R)-2-((R)-1-Amino-2-hydroxy-ethyl)-1-benzyl-4-oxo-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 110289-27-5 cis-(3R,4R)-1-benzyl-4-formyl-3-<(4R)-2-oxo-4-phenyloxazolidin-3-yl>azetidin-2-one 
• 135821-30-6 (4R,3'R,4'R)-3-<4'-(hydroxymethyl)-2'-oxo-1'-(phenylmethyl)-3'-azetidinyl>-4-phenyl-2-oxazolidinone 
• 144492-64-8 (3S,4S)-3-amino-1-benzyl-4-<(R)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl>azetidin-2-one 
• 234755-06-7 acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester 

Relevant academic research and scientific papers

Alkylidenecarbene insertion into a nitrogen lone pair: An unexpected synthesis of dihydropyrroles from alkynyliodonium salts

A novel intramolecular reaction between an alkylidenecarbene and the lone pair of electrons on a carbamate's nitrogen is described. The reaction occurs preferentially over an available 1,5 C-H insertion and gives substituted dihydropyrroles upon workup.

N,Se-Acetals: Preparation and Use in Diastereoselective Radical Reactions

A new facile synthesis of N,S- and N,Se-acetals starting from aldehydes and primary amines is presented (Schemes 3-5). These acetals are used as precursors for stereoselective radical deuteration and allylation reactions (Schemes 6 and 7, Tables 1 and 2). The stereochemical outcome of the reactions depends on the radical trap and the substituents at the N-atom. Deuterations give always anti products with moderate to high selectivities. The allylation reactions give either syn or anti products with low to moderate selectivities. The observed stereoselectivities can be explained with a model based on minimization of A1,3 strain and are controlled by steric and stereoelectronic effects.

N,Se-acetals: Easy preparation and application to radical mediated EPC synthesis

A facile synthesis of N,S- and N,Se-acetals starting from aldehydes and primary amines is presented. These acetals are used as precursors for radical reactions. The stereoselectivity of the reactions depends on the radical trap used.

Diastereoface Discrimination in the Addition of Acetylide to a Chiral Aldehyde, Leading to a Synthesis of (+)-Deoxybiotin in Enantiomerically Pure Form Starting from L-Cysteine

Complete diastereofacial discrimination was observed upon addition of the chlorozinc acetylide derived from 1-hexyne to a chiral aldehyde prepared from L-cysteine.The addition product was used in a short synthesis of (+)-deoxybiotin, a precursor of (+)-bi