Premium
One‐Pot Enantioselective Synthesis of 3‐Nitro‐2 H ‐chromenes Catalyzed by a Simple 4‐Hydroxyprolinamide with 4‐Nitrophenol as Cocatalyst
Author(s) -
Yin Guohui,
Zhang Richeng,
Li Lei,
Tian Jun,
Chen Ligong
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300505
Subject(s) - chemistry , nitro , salicylaldehyde , enantioselective synthesis , domino , catalysis , nitrophenol , nitroaldol reaction , michael reaction , medicinal chemistry , cascade reaction , organic chemistry , combinatorial chemistry , stereochemistry , schiff base , alkyl
The asymmetric domino oxa‐Michael–Henry reaction of salicylaldehyde derivatives with trans ‐β‐nitro olefins catalyzed by a readily available trans ‐4‐hydroxy‐ L ‐prolinamide with 4‐nitrophenol as an effective cocatalyst is presented. The corresponding 3‐nitro‐2 H ‐chromenes were obtained in moderate to excellent yields (up to 99 %) and with up to 90 % ee under mild conditions. In addition, a preliminary study shows that this organocatalytic system is able to promote the domino aza‐Michael–Henry reaction of 2‐formylpyrrole derivatives with trans ‐β‐nitro olefins to give chiral 2‐nitro‐3 H ‐pyrrolizines.