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. Author manuscript; available in PMC: 2015 Feb 27.
Published in final edited form as: J Am Chem Soc. 2014 Feb 27;136(10):3788–3791. doi: 10.1021/ja500706v

Table 1. Catalytic Enantioselective Cyclization/Cross-Coupling with an Alkyl Electrophile: Influence of Reaction Parametersa.

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entry variation from the “standard” conditions ee (%) yield (%)b
1 none 96 82
2 no NiBr2 • glyme <5
3 no (S,S)–1 <5
4 no i-BuOH <5
5 1.5 equiv of arylboron reagent 81 67
6 (S,S)–2, instead of (S,S)–1 39 64
7 (S,S)–3, instead of (S,S)–1 <5
8 (S,S)–4, instead of (S,S)–1 61 33
9 BnCH2CH2Cl, instead of BnCH2CH2Br <5
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a

All data are the average of two experiments.

b

The yield was determined by GC analysis with the aid of a calibrated internal standard.