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Enantioselective Synthesis of Oxindole‐Derived α‐Aryl‐β‐Amino Acid Derivatives and δ‐Lactams with Homophthalic Anhydrides
Author(s) -
Chang Zhixin,
Ye Can,
Fu Junfeng,
Chigumbu Paidamoyo,
Zeng Xiaofei,
Wang Yongjiang,
Jiang Chengjun,
Han Xiaoyu
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901074
Subject(s) - chemistry , enantioselective synthesis , stereocenter , oxindole , isatin , mannich reaction , stereoselectivity , aryl , adduct , lactam , stereochemistry , organic chemistry , catalysis , alkyl
A highly diastereo‐ and enantioselective Mannich reaction of isatin‐derived N ‐Boc imines with homophthalic anhydrides is disclosed for the first time, which allows the direct synthesis of a wide range of oxindole‐derived α‐aryl‐β‐amino acids with two adjacent carbon stereogenic centers in a highly stereoselective fashion (up to >95:5 dr & >99% ee). The resulted Mannich adducts can be easily converted to chiral spirocyclic δ‐lactams with retention of the stereoslectivities.