228098-63-3Relevant academic research and scientific papers
Highly efficient asymmetric access to 1-azaspiro[4.4]nonane skeleton
Planas, Lo?c,Pérard-Viret, Jo?lle,Royer, Jacques,Selkti, Mohamed,Thomas, Alain
, p. 1629 - 1632 (2007/10/03)
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
Dudot, Bruno,Royer, Jacques,Sevrin, Mireille,George, Pascal
, p. 4367 - 4371 (2007/10/03)
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
Dudot, Bruno,Micouin, Laurent,Baussanne, Isabelle,Royer, Jacques
, p. 688 - 694 (2007/10/03)
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.
