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Synfacts 2016; 12(1): 0071
DOI: 10.1055/s-0035-1561027
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective α-Alkylation of α-Epoxy N-Sulfonyl Hydrazones

Contributor(s):
Paul Knochel
,
Diana Haas
Uteuliyev MM, Nguyen TT, Coltart DM * University of Houston, USA
Diastereoselective Addition of Grignard Reagents to α-Epoxy N-Sulfonyl Hydrazones.

Nature Chem. 2015;
7: 1024-1027
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Further Information

Publication History

Publication Date:
16 December 2015 (online)

 
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Key words

Grignard reaction - epoxides - addition

Significance

Coltart and co-workers report the diastereoselective addition of Grignard reagents to α-epoxy N-sulfonyl hydrazones to give various β-hydroxy N-sulfonyl hydrazones with quaternary α-stereocenters in very high yields.


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Comment

The alkoxide, which is generated in situ through base-induced ring-opening of the epoxide, selectively directs the addition syn in a 1,4-manner.


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