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Only the trans compounds were formed in all reactions. The final products were formed via hydrolysis of the boron enolates; see the Supporting Information. In the boron enolates, the bulky aryl substituent on the sulfinyl group would be arranged in a position opposite to the added alkyl group by avoiding the steric interaction, and hydrolysis of the boron enolates occurs from the side opposite to the aryl group to give the trans compounds; see also ref 3a.
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45
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0006073827
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4 was added to hydrolyze the boron enolate without addition of acetic acid, excess triethylborane generated vast numbers of radicals on exposure to a large amount of oxygen to give unidentified products probably derived from the unreacted compound (4S)-4a or (5S)-4b. Acetic acid is known to react with trialkylborane; see: Brown, H. C.; Murray, K. J. Am. Chem. Soc. 1959, 81, 4108.
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