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Reactions of 2‐Amino‐1,3‐butadienes and Fischer Alkynyl Carbenes: Up to Nine C−C Bonds and Seven Stereogenic Centers Created in a Stereoselective Manner through a Cascade Process
Author(s) -
Barluenga José,
Aznar Fernando,
Barluenga Sofía,
Fernández Mónica,
Martín Alfredo,
GarcíaGranda Santiago,
PiñeraNicolás Alejandro
Publication year - 1998
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19981102)4:11<2280::aid-chem2280>3.0.co;2-#
Subject(s) - stereocenter , stereoselectivity , cascade , stereochemistry , chemistry , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis , chromatography
New reactions of alkynylcarbene complexes with 2‐amino‐1,3‐dienes are reported. The reactions involve a first [4+2] cycloaddition step followed by a cyclopentannulation process that generates a molecule containing a cyclopentadiene moiety capable of undergoing a new [4+2] cycloaddition reaction with the carbene complex. The process can be controlled to produce one, two or three cycloaddition–cyclopentannulation cycles (see Equation) in order to synthesize molecules from fluorenes to complex polycyclic scaffolds.