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Derivatives of (2 R )‐ N ‐Glyoxylbornane‐10,2‐sultam and Their Use as auxiliaries in the diastereoselective spirocyclization of 2‐substituted tryptamines
Author(s) -
Freund Ralf,
Allagiannis Christos,
Schönholzer Peter,
Bernauer Karl
Publication year - 1994
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.19940770304
Subject(s) - chemistry , hemiacetal , hydrate , dimer , tryptamines , halide , medicinal chemistry , stereochemistry , organic chemistry , tryptamine , biochemistry
A crude hydrate 6 and a crystalline hemiacetal 7 of glyoxylamide 4 were prepared from crotonamide 5 ( Scheme 2 ). Particularly hemiacetal 7 , but also 6 and the ‘dimer’ 8 (obtained from 7 ) may serve as homochiral auxiliaries. The structure of 8 was determined by X‐ray analysis. By arenesulfonyl halides, tryptimines 12–14 of 4 were diastereoselectively transformed into spirotricycles 15–17 and 19 .