N‐Alkoxyacrylamides in Domino Reactions: Catalytic and Stereoselective Access to δ‐Lactams

Abstract

The first domino aza-Michael/intramolecular-Michael reaction employing acrylamides as key ambivalent partners for the synthesis of δ-lactams is presented. It has been shown that the desired reactivity is contingent to the presence of an N- [a]

Highly Efficient and Diastereoselective Construction of Substituted Pyrrolidines Bearing A Quaternary Carbon Center via 1,3-Dipolar [3 + 2] Cycloaddition

“…The reaction afforded the corresponding products 3 (3a-p) in high isolated yields (92-98%) with excellent diastereoselectivities (>25:1 dr). Additionally, the effect of the sulfonyl group of cyanosulfone 1q [39][40] and 1r [41][42][43][44][45] was studied to give the corresponding products 3q and 3r in 95% and 95% yields, respectively. It's worth noting that the cycloaddition reaction was also amenable to the present system, and a similar degree of diastereoselectivities was observed when the cyano group or ester group instead of the sulfonyl group (entries [19][20].…”

20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions

“…Replacing K2CO3 with Na2CO3 led to no conversion when treatment with MeONa in MeOH or t-BuOK in THF turned the reaction into a complex mixture. 54 In the presence of a catalytic amount of K2CO3 (20 mol %) in CH3CN, the desired cyclic products 32 were isolated in yields ranging from 40 to 84%. Moreover, up to 3 stereocenters could be forged during the process with dr up to 98:2.…”

“…More recently, Comesse and co-workers developed a catalytic and stereoselective intermolecular domino aza-Michael/Michael reaction leading to highly functionalized -lactams 32 in good yields and stereocontrol under mild conditions (Scheme 10). 54 In the presence of a catalytic amount of K 2 CO 3 (20 mol%) in CH 3 CN, the desired cyclic products 32 were isolated in yields ranging from 40-84%. Moreover, up to 3 stereocenters could be forged during the process, with dr values of up to 98:2 being obtained.…”

Probing N‐Alkoxy Effects in Domino Reactions of α‐Bromoacetamide Derivatives Towards Functionalized γ‐Lactams

“…3). [9] Good yields of the desired products were obtained from N-alkoxyacrylamides 8 (R 1 = alkoxy) but no reaction was observed when N-alkylacrylamides (R 1 = alkyl) were employed. These first observations prompted us to re-examine some of our earlier works on the synthesis of γ-lactams 11, [10] employing this time N-alkoxyhaloamides 1 compared to the original Nalkyl congeners (Scheme 1, eq.…”