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One-pot synthesis of lactams using domino reactions: combination of Schmidt reaction with Sakurai and aldol reactions.

ABSTRACT: A series of domino reactions in which the intramolecular Schmidt reaction is combined with either a Sakurai reaction, an aldol reaction, or both is reported. The Sakurai reaction of an allylsilane with an azido-containing enone under Lewis acidic conditions followed by protonation of the resulting titanium enolate species allowed for a subsequent intramolecular Schmidt reaction. Alternatively, the intermediate titanium enolate could undergo an aldol reaction followed by the intramolecular Schmidt reaction to form lactam products with multiple stereogenic centers. The stereochemical features of the titanium enolate aldol reaction with several 3-azidoaldehyde substrates during this domino process is discussed.

SUBMITTER: Huh CW

PROVIDER: S-EPMC2778731 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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One-pot synthesis of lactams using domino reactions: combination of Schmidt reaction with Sakurai and aldol reactions.

Huh Chan Woo CW Somal Gagandeep K GK Katz Christopher E CE Pei Huaxing H Zeng Yibin Y Douglas Justin T JT Aubé Jeffrey J

The Journal of organic chemistry 20091001 20

A series of domino reactions in which the intramolecular Schmidt reaction is combined with either a Sakurai reaction, an aldol reaction, or both is reported. The Sakurai reaction of an allylsilane with an azido-containing enone under Lewis acidic conditions followed by protonation of the resulting titanium enolate species allowed for a subsequent intramolecular Schmidt reaction. Alternatively, the intermediate titanium enolate could undergo an aldol reaction followed by the intramolecular Schmid ...[more]

PMID: 19761271

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