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Tandem application of C-C bond-forming reactions with reductive ozonolysis.

ABSTRACT: Several variants of reductive ozonolysis, defined here as the in situ generation of aldehydes or ketones during ozonolytic cleavage of alkenes, are demonstrated to work effectively in tandem with a number of C-C bond-forming reactions. For reactions involving basic nucleophiles (1,2-addition of Grignard reagents, Wittig or Horner-Emmons olefinations, and directed aldol reactions of lithium enolates), the one-pot process offers a rapid and high-yielding alternative to traditional two-step protocols.

SUBMITTER: Willand-Charnley R

PROVIDER: S-EPMC3537893 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Tandem application of C-C bond-forming reactions with reductive ozonolysis.

Willand-Charnley Rachel R Dussault Patrick H PH

The Journal of organic chemistry 20121002 1

Several variants of reductive ozonolysis, defined here as the in situ generation of aldehydes or ketones during ozonolytic cleavage of alkenes, are demonstrated to work effectively in tandem with a number of C-C bond-forming reactions. For reactions involving basic nucleophiles (1,2-addition of Grignard reagents, Wittig or Horner-Emmons olefinations, and directed aldol reactions of lithium enolates), the one-pot process offers a rapid and high-yielding alternative to traditional two-step protoco ...[more]

PMID: 22994627

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