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Inside Cover: Highly Stereoselective [4+2] and [3+2] Spiroannulations of 2‐(2‐Oxoindolin‐3‐ylidene)acetic Esters Catalyzed by Bifunctional Thioureas (Chem. Eur. J. 31/2015)
Author(s) -
Monari Magda,
Montroni Elisa,
Nitti Andrea,
Lombardo Marco,
Trombini Claudio,
Quintavalla Arianna
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201590138
Subject(s) - bifunctional , stereocenter , thiourea , catalysis , chemistry , stereoselectivity , combinatorial chemistry , nitro , cascade reaction , organocatalysis , medicinal chemistry , organic chemistry , stereochemistry , enantioselective synthesis , alkyl
An efficient synthesis of β‐nitro spirocarbocyclic oxindoles containing multiple stereocenters has been developed mediated by thiourea‐based bifunctional organocatalysts, such as Takemoto's catalyst (TUC), as reported by A. Quintavalla et al. in their Full Paper on page 11038 ff. The catalyst promotes a cascade spiroannulation, starting from 3‐ylidene oxindoles and nitroenoates. A wide range of products is obtained in good yields and high stereocontrol. Depending on the nitro compound, both 5‐ and 6‐membered spirooxindoles are accessible. Furthermore, the nitroenoate double bond configuration determines the absolute configuration of the spiro center.