Synthesis of amido-spiro[2.2]pentanes via Simmons–Smith cyclopropanation of allenamides

Ting Lu; Ryuji Hayashi; Richard P. Hsung; Kyle A. DeKorver; Andrew G. Lohse; Zhenlei Song; Yu Tang

doi:10.1039/B908205K

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Organic & Biomolecular Chemistry

Issue 16, 2009

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Synthesis of amido-spiro[2.2]pentanes via Simmons–Smith cyclopropanation of allenamides

Ting Lu , Ryuji Hayashi , Richard P. Hsung , Kyle A. DeKorver , Andrew G. Lohse , Zhenlei Song and Yu Tang

Org. Biomol. Chem., 2009, 7, 3331-3337

DOI: 10.1039/B908205K
Received 27 Apr 2009, Accepted 19 May 2009
First published on the web 19 Jun 2009

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A detailed account of Simmons–Smith cyclopropanations of allenamides en route to amido-spiro[2.2]pentanes is described here. While the diastereoselectivity was low when using unsubstituted allenamides, the reaction is overall efficient and general, representing the most direct synthesis of both chemically and biologically interesting amido-spiro[2.2]pentane systems. With α-substituted allenamides, while the diastereoselectivity could be improved significantly based on a series of conformational analyses, both mono- and bis-cyclopropanation products were observed. Consequently, several structurally intriguing amido-methylene cyclopropanes could also be prepared.

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Experimental procedures, ¹H NMR spectra, and characterizations for all newcompounds
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Ting Lu
Ryuji Hayashi
Richard P. Hsung
Kyle A. DeKorver
Andrew G. Lohse
Zhenlei Song
Yu Tang

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Organic & Biomolecular Chemistry

Synthesis of amido-spiro[2.2]pentanes via Simmons–Smith cyclopropanation of allenamides

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