Yttrium-Catalyzed C(sp3)–H Addition to Cyclopropenes

Mark Lautens; Nicolas Zeidan

doi:10.1055/s-0036-1591261

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Synfacts 2017; 13(10): 1051
DOI: 10.1055/s-0036-1591261

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Yttrium-Catalyzed C(sp³)–H Addition to Cyclopropenes

Contributor(s):

Mark Lautens

,

Nicolas Zeidan

Luo Y. Teng H.-L. Nishiura M. Hou Z. * RIKEN, Saitama, Japan
Asymmetric Yttrium-Catalyzed C(sp³)–H Addition of 2-Methyl Azaarenes to Cyclopropenes.

Angew. Chem. Int. Ed. 2017;
56: 9207-9210

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Further Information

Publication History

Publication Date:
18 September 2017 (online)

Abstract
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Key words

yttrium catalysis - azaarenes - cyclopropenes

Significance

Hou and co-workers disclosed a novel asymmetric C(sp³)–H addition to cyclopropenes and norbornenes. The reaction provides complex cyclopropanes and norbornanes in high yield with good to excellent enantio- and diastereoselectivity.

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Comment

The proposed mechanism of the transformation involves the activation of an yttrium precatalyst by alkyl abstraction and metal-assisted deprotonation of the substrate. The cycle commences with carbometalation, and subsequent deprotonation of a second substrate completes the catalytic cycle.

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