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Ethylenebis(sulfonyl)‐bridged 1,1′‐Binaphthalene, an Atropisomeric Dienophile for Highly Diastereoselective Diels‐Alder Reactions
Author(s) -
Cossu Sergio,
Delogu Giovanna,
De Lucchi Ottorino,
Fabbri Davide,
Licini Giulia
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198907661
Subject(s) - acetylene , adduct , sulfonyl , chemistry , derivative (finance) , diels–alder reaction , stereospecificity , polymer chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl , financial economics , economics
The 1,1′‐binaphthalene derivative 1 is the first acetylene equivalent developed for asymmetric Diels–Alder reactions. It reacts at room temperature with a variety of unsymmetric dienes in a nearly stereospecific fashion. The initial adducts can be cleaved with sodium amalgam to give products corresponding to those formally obtained by acetylene addition to dienes.