80365-68-0Relevant academic research and scientific papers
Palladium-catalyzed asymmetric allylic alkylation of acyclic ketones for synthesis of 2,2-disubsituted pyrrolidine derivatives
Lian, Wen-Fang,Wang, Cui-Cui,Kang, Huai-Ping,Li, Hai-Ling,Feng, Juan,Liu, Shouxin,Zhang, Zhi-Wei
, p. 1399 - 1402 (2017/03/17)
Palladium-catalyzed asymmetric allylic alkylation of acyclic ketones represents a significant challenge in organic synthesis. We report herein that the synthesis of chiral 2,2-disubsituted pyrrolidines from acyclic ketones has been accomplished by using catalytic asymmetric method in the presence of Pd(dba)2 and (R)-binap ligand. Theses reactions occur between allyl methyl carbonate and unstabilized acyclic lithium enolates to provide the products in moderate to good enantioselectivity (up to 81% ee).
One-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: A simple route to substituted pyrrolidines
Bott, Tina M.,Vanecko, John A.,West
supporting information; experimental part, p. 2832 - 2836 (2009/08/15)
Simple N-substituted azetidines were heated with diazocarbonyl compounds in the presence of catalytic Cu(acac)2 to furnish substituted pyrrolidines via Stevens [1,2]-shift. In all but two examples, complete selectivity was seen for ring expansion rather than migration of the other exocyclic group on the azetidinium nitrogen. The two exceptions, observed with ylides substituted with two carbonyl groups and lacking a stabilizing group at the 2-position of the azetidine, underwent exocyclic benzyl migration in preference to ring expansion.
