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Iron‐Mediated Diastereoselective Spiroannelation to the Spiro[1,2,3,4‐tetrahydroquinoline‐4,1′‐cyclohexane] System and a Novel Rearrangement to 2,3‐Dihydroindole Derivatives
Author(s) -
Knölker HansJoachim,
Boese Rolaid,
Hartmann Konrad
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.198916781
Subject(s) - cyclohexane , ring (chemistry) , derivative (finance) , component (thermodynamics) , aryl , chemistry , medicinal chemistry , unit (ring theory) , group (periodic table) , organic chemistry , mathematics , physics , thermodynamics , business , alkyl , mathematics education , finance
Attack anti to the Fe(CO) 3 group during spiroannelation (a) causes the aryl ring to be transformed into a cyclohexadiene unit. Demetallation of 1 gives either the free spiroheterocycle or a 2,3‐dihydroindole derivative. The spiroheterocyclic framework of 1 is an important component of several natural products.