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Synfacts 2015; 11(3): 0299
DOI: 10.1055/s-0034-1380029
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Directed Metalation of Ester-Substituted Indolizines

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Amaral MF. Z. J, Baumgartner AA, Vessecchi R, Clososki GC * Universidade de São Paulo, Ribeirão Preto, Brazil
Directed Metalation of 1-Ester-Substituted Indolizines: Base/Electrophile-Controlled Regioselective Functionalization.

Org. Lett. 2015;
17: 238-241
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Further Information

Publication History

Publication Date:
16 February 2015 (online)

 
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Key words

metalation - magnesium - indolizines

Significance

Clososki and co-workers report a directed C–H functionalization of 1-ester-substituted indolizines using several organometallic bases. The metalation takes place under mild conditions, and the reaction with different electrophiles allows the synthesis of a number of polyfunctional indolizines in good yields.


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Comment

Lithium amides favor C-5 functionalization, while TMPMgCl·LiCl gives C-2 substituted derivatives as major products by ortho metalation. The authors found that in the case of functionalization with TMPMgCl·LiCl, the reactivity of the electrophile plays a key role in the regioselectivity of the reaction.


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