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2005
Fused pyrrole derivatives
R 0160
Heterocyclic α-Alkylidene Cyclopentenones Obtained via a Pauson—Khand Reof Amino Acid Derived Allenynes. A Scope and Limitation Study Directed
31- 128 action
Toward the Preparation of a Tricyclic Pyrrole Library. — A concise route to tricyclic pyrroles is developed using a Pauson—Khand, Stetter, Paal—Knorr reaction sequence. In the Pauson—Khand reaction, an unprecedented substitution effect on the diastereoselectivity is observed. Aryl- and alkyl-substituted substrates lead to opposite
diastereomers. The Pall—Knorr cyclization proceeds successfully with a range of
amines but some limitations are found. Unfortunately, epimerization at C-7 takes place
and products bearing a 2-alkyl group such as (XIVa) are not stable. —
(BRUMMOND*, K. M.; CURRAN, D. P.; MITASEV, B.; FISCHER, S.; J. Org.
Chem. 70 (2005) 5, 1745-1753; Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260,
USA; Eng.) — Jannicke
2005
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