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An Enantio‐ and Diastereoselective Mannich/Pictet–Spengler Sequence To Form Spiro[piperidine‐pyridoindoles] and Application to Library Synthesis
Author(s) -
RiescoDomínguez Alejandra,
van der Zwaluw Nick,
BlancoAnia Daniel,
Rutjes Floris P. J. T.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601508
Subject(s) - pictet–spengler reaction , piperidine , chemistry , enantioselective synthesis , tryptamine , mannich reaction , sequence (biology) , stereochemistry , combinatorial chemistry , tandem , organic chemistry , catalysis , materials science , composite material , biochemistry
A new tandem strategy based on a Mannich/Pictet–Spengler sequence has been developed and applied to the synthesis of a new small library (14 examples) of privileged compounds based on the spiro[piperidine‐pyridoindole] core. The sequence proceeds by a diastereoselective Pictet–Spengler cyclization after condensation of several tryptamine derivatives with three novel piperidin‐4‐ones containing the fluorinated substituents F, CF 3 and SF 5 . The piperidin‐4‐ones were synthesized from readily available starting materials by an enantioselective multi‐component organocatalytic Mannich reaction.