62030-44-8

Upstream product

• 33574-02-6 cyclopropylmethyl iodide 
• 108-23-6 isopropyl chloroformate 
• 591-80-0 pent-4-enoic acid 
• 67-63-0 isopropyl alcohol 
• 1772-43-6 2,4,4-trimethyl oxazoline 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 1583259-44-2 (2R,3S,4R)-isopropyl 2-allyl-5-(benzyloxy)-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 
• 1583259-43-1 (2S,3S,4R)-isopropyl 2-allyl-5-(benzyloxy)-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 

Relevant academic research and scientific papers

Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes

Radical hydrofunctionalization occurs with ease using metal-hydride hydrogen atom transfer (MHAT) catalysis to couple alkenes and competent radicalophilic electrophiles. Traditional two-electron electrophiles have remained unreactive. Herein we report the reductive coupling of electronically unbiased olefins with imines and aldehydes. Iron catalysis allows addition of alkyl-substituted olefins into imines through the intermediacy of free radicals, whereas a combination of catalytic Co(Salt-Bu,t-Bu) and chromium salts enables a branch-selective coupling of olefins and aldehydes through the formation of a putative alkyl chromium intermediate.

Ester Formation via Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Chloroformates

The synthesis of alkyl esters from readily available alkyl halides and chloroformates was achieved for the first time using a mild Ni-catalyzed reductive coupling protocol. Unactivated primary and secondary alkyl iodides as well as glycosyl, benzyl, and aminomethyl halides were successfully employed to yield products in moderate to excellent yields with high functional group tolerance.

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.