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Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.

ABSTRACT: Enzymes are a continuing source of inspiration for the design of new chemical reactions that proceed with efficiency, high selectivity and minimal waste. In many biochemical processes, different catalytic species, such as Lewis acids and bases, are involved in precisely orchestrated interactions to activate reactants simultaneously or sequentially. This type of 'cooperative catalysis', in which two or more catalytic cycles operate concurrently to achieve one overall transformation, has great potential in enhancing known reactivity and driving the development of new chemical reactions with high value. In this disclosure, a cooperative N-heterocyclic carbene/Lewis acid catalytic system promotes the addition of homoenolate equivalents to hydrazones, generating highly substituted gamma-lactams in moderate to good yields and with high levels of diastereo- and enantioselectivity.

SUBMITTER: Raup DE

PROVIDER: S-EPMC2928160 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.

Raup Dustin E A DE Cardinal-David Benoit B Holte Dane D Scheidt Karl A KA

Nature chemistry 20100718 9

Enzymes are a continuing source of inspiration for the design of new chemical reactions that proceed with efficiency, high selectivity and minimal waste. In many biochemical processes, different catalytic species, such as Lewis acids and bases, are involved in precisely orchestrated interactions to activate reactants simultaneously or sequentially. This type of 'cooperative catalysis', in which two or more catalytic cycles operate concurrently to achieve one overall transformation, has great pot ...[more]

PMID: 20729898

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