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Diastereoselective Spirocyclization of Imines of 2‐Substituted 1 H ‐Indole‐3‐ethylamines ( = Trypatamines): Variation of the electrophile and the substituent at C(2) and its influence on the steric outcome. 6th Communication on indoles, indolenines, and indolines
Author(s) -
Freund Ralf,
Martinović Suzanna,
Bernauer Karl
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750124
Subject(s) - chemistry , steric effects , substituent , electrophile , indole test , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Tryptimines of type 7 form with various acyl halogenides EX preferentially tricycles of type 8 ( cf: Scheme 2 ). The homochiral imines 9 and 17 are transformed into (2′ R ,3 S )‐configurated products. The synthetic and mechanistic importance of these results is discussed.