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Synfacts 2014; 10(8): 0838
DOI: 10.1055/s-0034-1378414
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Intramolecular [3+2] Annulation

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Zhu J, Liang Y, Wang L, Zheng Z.-B, Houk KN, * Tang Y. * Shanghai Institute of Organic Chemistry, P. R. of China and University of California, Los Angeles, USA
Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines.

J. Am. Chem. Soc. 2014;
136: 6900-6903
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Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

copper - diimine ligands - spiroindolines

Significance

Spirocyclic indoline-based structures are highly privileged and constitute a number of natural products and biologically active compounds. As such, their stereoselective synthesis is a prime target for developing new synthetic methodologies. The authors report a copper-catalyzed intramolecular [3+2] annulation of indoles tethered to a cyclopropane.


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Comment

An interesting switch in the stereochemistry of the products was observed when the ester groups were modified. With an isopropyl ester, the trans isomer (with respect to the two hydrogens) was observed. Switching to an adamantyl ester gave the cis isomer.


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