Stereoselective Synthesis of Annelated Piperidines by Photochemical Cycloaddition and Iminium IonAllylsilane Cyclization | Zendy

Tietze Lutz F. | Zendy; Wünsch Josef R. | Zendy

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Stereoselective Synthesis of Annelated Piperidines by Photochemical Cycloaddition and Iminium IonAllylsilane Cyclization

Author(s) -

Tietze Lutz F.,

Wünsch Josef R.

Publication year - 1991

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.199116971

Subject(s) - iminium , cycloaddition , chemistry , diastereomer , enamine , stereoselectivity , medicinal chemistry , ion , stereochemistry , organic chemistry , catalysis

Only one of eight possible diastereomers is produced on treatment of enamine carbaldehydes 1 (RH, CH 3 , p ‐MeOC 6 H 5 CH 2 ) with alkenes 2 ( n = 1, 2) that contain electron acceptor and allylsilane groups. A photochemical cycloaddition yields the 2‐hydroxytetrahydropyridine 3 , which cyclizes on addition of acids to the azabicycles 4. In the iminium ion intermediate stage, the allylsilane group attacks C2 anti to the H atom bound to C3.

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