263722-10-7

Upstream product

• 536-74-3 phenylacetylene 
• 164530-43-2 Weinreb amide 
• 4440-01-1 lithium phenylacetylide 

Downstream Products

• 263722-14-1 [2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(1-hydroxy-3-phenyl-prop-2-enyl)-4-phenyl-1,3-oxazolidine 
• 263722-12-9 [2R,2(1S),4R]-3-tert-butoxycarbonyl-2-(1-hydroxy-3-phenyl-prop-2-ynyl)-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.

Claisen rearrangement of allylic alcohols prepared through N-Boc-2-acyloxazolidine methodology. Application to the synthesis of trisubstituted cyclopropanes

Stereodefined allylic alcohols prepared from a (R)-phenylglycinol-derived Weinreb amide undergo a Claisen rearrangement with a high level of stereocontrol. The produced N-Boc-2-alcenyloxazolidines can be either hydrolyzed to afford enantiomerically enriched enals or further epoxidized using a two-step sequence. The resulting epoxyoxazolidines can then be transformed into trisubstituted cyclopropanes. (C) 2000 Elsevier Science Ltd.