228098-63-3

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 98-88-4 benzoyl chloride 
• 228098-62-2 (2R)-2-(2,5-Dihydro-2-oxopyrrol-1-yl)-2-phenylethylbenzoate 

Downstream Products

• 639503-02-9 2-{(S)-[(R)-1-((R)-2-Benzoyloxy-1-phenyl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl]-hydroxy-methyl}-benzoic acid methyl ester 

Relevant academic research and scientific papers

Highly efficient asymmetric access to 1-azaspiro[4.4]nonane skeleton

Vinylogous Mukaiyama aldol type reaction of chiral non-racemic silyloxypyrroles followed by acidic treatment affords an efficient asymmetric access to 1-azaspiro[4.4]nonanes in high diastereoisomeric excess (up to 79%).

Ytterbium triflate-catalyzed reactions of imines with a chiral non- racemic silyloxypyrrole

In the presence of a catalytic amount of ytterbium triflate the reactions of various aromatic imines with a chiral non-racemic silyloxypyrrole proceeded smoothly to afford the corresponding aldol-type adducts in good yields and diastereoselectivities. (C)

Asymmetric routes towards polyfunctionalized pyrrolidines: A short diastereoselective synthesis of polyhydroxylated pyrrolidines and an indolizidine

Various (2S,3S,4R)-2-[(1R)-1-hydroxyalkyl]pyrrolidine-3,4-diols (11) have been prepared in 8 steps and 13-20% overall yield starting from (R)-(- )-phenylglycinol. This concise approach is based on the condensation of a chiral silyloxypyrrole with aldehydes which gave the (R,R)-aldol compounds in good yields and high diastereoselectivities. The cis-hydroxylation followed by reduction and deprotection gave the desired trihydroxylated pyrrolidines. The same strategy has been successively applied to a formal synthesis of 8a- epi-swainsonine.