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. Author manuscript; available in PMC: 2010 Aug 19.
Published in final edited form as: J Am Chem Soc. 2009 Aug 19;131(32):11625–11633. doi: 10.1021/ja904654j

Table 4.

Initial Studies on Allylic Alkylations with Me3Al in the Presence of N-Heterocyclic Lewis Base Catalystsa

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entry Lewis base; (mol %) conv (%)b SN2′:SN2b erc
1 none 5 62:38
2 6a; 5 10 80:20 66.5:33.5
3 6b; 5 <2
4 7; 2.5 <2
a

Reactions were performed under N2 atmosphere.

b

Conversion and site-selectivity were determined by analysis of 400 MHz 1H NMR spectra of product mixtures prior to purification.

c

Enantiomer ratios were determined by GLC analysis; see the Supporting Information for details.