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Practical asymmetric Mukaiyama-Michael reaction of benzalacetone derivatives catalyzed by allo-threonine-derived oxazaborolidinone

✍ Scribed by Xiaowei Wang; Toshiro Harada; Hiroyoshi Iwai; Akira Oku

Publisher: John Wiley and Sons
Year: 2002
Tongue: English
Weight: 59 KB
Volume: 15
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.10161

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✦ Synopsis

In the presence of 2,6-diisopropylphenol and t-BuOMe (1 equiv. each), asymmetric Mukaiyama-Michael reaction of a variety of benzalacetone derivatives 2 with silyl ketene acetal 3 is efficiently catalyzed by O-(2-naphthoyl)-N-tosyl-(L)-allo-threonine-derived B-phenyloxazaborolidinone 1 (10 mol%) to give the corresponding adducts 5 in 60-90% ee.

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