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Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

ABSTRACT: A highly enantioselective carboalkoxylation of alkynes catalyzed by cationic (DTBM-MeO-Biphep)gold(I) complexes is reported. Various optically active ?-alkoxyindanone derivatives were obtained in good yields with high enantioselectivities. Furthermore, this methodology was extended to the enantioselective synthesis of 3-methoxycyclopentenones. The reaction is proposed to proceed through an enantioselective cyclization of intermediates containing vinylgold(I) and prochiral oxocarbenium moieties.

SUBMITTER: Zi W 

PROVIDER: S-EPMC3795527 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Zi Weiwei W   Toste F Dean FD  

Journal of the American Chemical Society 20130819 34

A highly enantioselective carboalkoxylation of alkynes catalyzed by cationic (DTBM-MeO-Biphep)gold(I) complexes is reported. Various optically active β-alkoxyindanone derivatives were obtained in good yields with high enantioselectivities. Furthermore, this methodology was extended to the enantioselective synthesis of 3-methoxycyclopentenones. The reaction is proposed to proceed through an enantioselective cyclization of intermediates containing vinylgold(I) and prochiral oxocarbenium moieties. ...[more]

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