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One‐Pot Formation of Functionalized Pyrrolinones and 2‐Oxohexahydroindoles from Aminocarbene Complexes of Chromium
Author(s) -
Rudler Henri,
Parlier Andrée,
Ousmer Malika,
Vaissermann Jacqueline
Publication year - 1999
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/(sici)1099-0690(199912)1999:12<3315::aid-ejoc3315>3.0.co;2-m
Subject(s) - chemistry , protonation , diphenylacetylene , pyridine , chromium , ylide , medicinal chemistry , triple bond , alkylation , acetic acid , hydride , polymer chemistry , organic chemistry , double bond , catalysis , ion , hydrogen
Aminocarbene complexes of chromium 1b‐d react successively with diphenylacetylene, XH (X = PhS, PhSe, OAc) and finally with pyridine to give a series of functionalized pyrrolinones 7 via N‐ylide complexes 2 . The X‐ray structure of 7b originating from a ring‐opening reaction could be established. When this sequence was applied to the aminocarbene complex 8 bearing a tethered triple bond, synthesis of functionalized 2‐oxohexahydroindole 11 was achieved. In the case of acetic acid, products resulting from a formal protonation/hydride addition reaction together with a carbon–nitrogen bond rupture were also observed besides protonation/dealkylation products.