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Sequential Transformation of Benzothiopyrylium Salts to Diastereoselectively Annulated Benzothiopyranones
Author(s) -
Beifuss Uwe,
Gehm Henning,
Noltemeyer Mathias,
Schmidt HansGeorg
Publication year - 1995
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.199506471
Subject(s) - stereocenter , intramolecular force , cascade , yield (engineering) , chemistry , transformation (genetics) , stereochemistry , cascade reaction , combinatorial chemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , chromatography , biochemistry , metallurgy , gene
As many as three stereogenic centers were introduced in one step in the preparatively simple cascade reaction of 1‐benzothiopyrylium salts with 2‐siloxy‐1,3‐butadienes. The cascade comprises 1,2‐additions and subsequent intramolecular 1,4‐additions and gives the all‐ cis ‐thioxanthon rac ‐ 3 in 91% yield from the starting compounds 1 and 2 , formed in situ. A diastereoselective synthesis of such compounds was not previously known.