Issue 11, 2017

A formal homo-Nazarov cyclization of enantioenriched donor–acceptor cyclopropanes and following transformations: asymmetric synthesis of multi-substituted dihydronaphthalenes

Abstract

Multi-substituted trans-dihydronaphthalenes were obtained in high enantiomeric excess from a TiCl4-mediated cyclization of enantioenriched donor–acceptor cyclopropanes, followed by a triflation of the hydroxy groups. The C–OTf bond in these multi-substituted trans-dihydronaphthalenes is susceptible to further Pd-catalyzed hydrogenations and coupling reactions, which afforded the corresponding C–H or C–C bonded products.

Graphical abstract: A formal homo-Nazarov cyclization of enantioenriched donor–acceptor cyclopropanes and following transformations: asymmetric synthesis of multi-substituted dihydronaphthalenes

Supplementary files

Article information

Article type
Paper
Submitted
06 Feb 2017
Accepted
24 Feb 2017
First published
24 Feb 2017

Org. Biomol. Chem., 2017,15, 2443-2449

A formal homo-Nazarov cyclization of enantioenriched donor–acceptor cyclopropanes and following transformations: asymmetric synthesis of multi-substituted dihydronaphthalenes

S. Takada, N. Takaki, K. Yamada and Y. Nishii, Org. Biomol. Chem., 2017, 15, 2443 DOI: 10.1039/C7OB00278E

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