Derivatives of (2 R )‐ N ‐Glyoxylbornane‐10,2‐sultam and Their Use as auxiliaries in the diastereoselective spirocyclization of 2‐substituted tryptamines | Zendy

Freund Ralf | Zendy; Allagiannis Christos | Zendy; Schönholzer Peter | Zendy; Bernauer Karl | Zendy

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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 .

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