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Issue 2, 2020
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Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes

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Abstract

Reports of C–H insertions forming six-membered rings containing heteroatoms are rare due to Stevens rearrangements occurring after nucleophilic attack on the carbene by a heteroatom. Using donor/donor carbenes and Rh2(R-PTAD)4 as a catalyst, we have synthesized a collection of isochroman substrates in good yield, with excellent diastereo- and enantioselectivity, and no rearrangement products were observed. Furthermore, we report the first synthesis of six-membered rings containing nitrogen by C–H insertion to form tetrahydroisoquinolines. In one case, a Stevens rearrangement product was isolated at elevated temperature from a carbamate-protected amine substrate and computational evidence suggests formation through a free ylide not bound to rhodium.

Graphical abstract: Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes

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Article information


Submitted
09 Oct 2019
Accepted
11 Nov 2019
First published
13 Nov 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 494-498
Article type
Edge Article

Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C–H insertion of donor/donor carbenes

L. A. Nickerson, B. D. Bergstrom, M. Gao, Y. Shiue, C. J. Laconsay, M. R. Culberson, W. A. Knauss, J. C. Fettinger, D. J. Tantillo and J. T. Shaw, Chem. Sci., 2020, 11, 494
DOI: 10.1039/C9SC05111B

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