Synthesis of l-threitol-based crown ethers and their application as enantioselective phase transfer catalyst in Michael additions.
作者： Zsolt Rapi , Tamás Nemcsok , Ádám Pálvölgyi , György Keglevich , Alajos Grün
DOI: 10.1002/CHIR.22678
关键词:
摘要: A few new l-threitol-based lariat ethers incorporating a monoaza-15-crown-5 unit were synthesized starting from diethyl l-tartrate. These macrocycles used as phase transfer catalysts in asymmetric Michael addition reactions under mild conditions to afford the adducts cases good excellent enantioselectivities. The of 2-nitropropane trans-chalcone, and reaction acetamidomalonate with β-nitrostyrene resulted chiral enantioselectivities (90% 95%, respectively). substituents chalcone had significant impact on yield enantioselectivity acetoxymalonate. highest enantiomeric excess (ee) values (99% ee) measured case 4-chloro- 4-methoxychalcone. catalyzed cyclopropanation benzylidene-malononitriles using bromomalonate nucleophile (MIRC reaction) was also developed. corresponding cyclopropane diesters obtained moderate (up 99%) presence threitol-based crown ethers.
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