234122-95-3

Upstream product

• 91509-32-9 3-(t-butyldimethylsilyloxy)prop-1-ynyllithium 
• 76782-82-6 tert-Butyldimethyl(prop-2-ynyloxy)silane 
• 179600-33-0 [2R,2(1S),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-hydroxy-but-2-ynyl)-4-phenyl-1,3-oxazolidine 
• 234122-92-0 (2R,4R)-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-but-2-ynoil)-4-phenyl-1,3-oxazolidine 
• 164530-43-2 Weinreb amide 

Downstream Products

• 234122-97-5 [2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine 
• 234123-03-6 [2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine 
• 263722-28-7 [3R,7S,7(1R),8S,9R]-8-bromo-7-(2-tert-butyldimethylsilyloxy-1-methylethyl)-3-phenyl-tetrahydrooxazolo[3,2-c][1,3]oxazin-5-one 
• 319002-41-0 (2R,4R)-2-[(1R,2R,3S)-4-tert-butyldimethylsilyloxy-1,2-epoxy-3-ethoxycarbonylmethylbutyl]-3-ethoxycarbonyl-4-phenyl-1,3-oxazolidine 
• 319002-39-6 (3R,7S,8S,9R)-8-bromo-7-[(1S)-2-tert-butyldimethylsilyloxy-1-ethoxycarbonylmethylethyl]-3-phenyltetrahydrooxazolo[3,2-c][1,3]oxazin-5-one 
• 319002-27-2 (2R,4R)-3-tert-butoxycarbonyl-2-[(1E,3R)-4-tert-butyldimethylsilyloxy-3-ethoxycarbonylmethylbut-1-enyl]-4-phenyl-1,3-oxazolidine 

Relevant academic research and scientific papers

S(N)2' regio and stereoselective alkylation of allylic and propargylic mesylates linked to a N-Boc oxazolidine using organocuprates

N-Boc-oxazolidines derived from (R)-phenylglycinol and bearing a stereodefined propargylic or allylic alcohol side chain were transformed into the corresponding mesylates. Alkylation of these allylic mesylates by means of organocuprate reagents effected a regio and stereoselective 1,3-transfer of chirality. Similarly, alkylation of the propargylic mesylate gave a chiral allenyl oxazolidine. The N-Boc-2-alkenyl oxazolidines resulting from an anti S(N)2' addition underwent an intramolecular bromocarbamoylation with a high level of stereocontrol upon treatment with NBS. After reaction with sodium alkoxide, the resulting cyclic urethanes gave the corresponding epoxy oxazolidines whose reactivity towards organocuprates was studied. The sequence represents an efficient synthesis of enantiopure protected aldehydes bearing three contiguous chiral centers. (C) 2000 Elsevier Science Ltd.

Sn2' regio and stereoselective alkylation of allylic mesylates linked to a N-Boc oxazolidine using organocuprates

N-Boc-oxazolidines bearing an allylic alcohol chain were transformed into their mesylate derivatives. A regio and stereoselective 1,3-transfer of chirality was effected on these mesylates during their alkylation by mean of organocuprate additions. The resulting N-Boc-2-alkenyl oxazolidines undergo an intramolecular bromocarbamoylation with a high level of stereocontrol upon treatment with bIBS and afford, after treatment with sodium ethoxide, the corresponding epoxy oxazolidines. The overall methodology allows an efficient control for the formation of three contiguous chiral centers.