Angewandte
Chemie
and stirred for 24 h, then a suspension of NaBO3·4H2O (10 equiv,
769 mg, 5 mmol) in H2O (6 mL) was added. After the mixture had
been stirred at RT for 24 h, it was poured into water, extracted with
Et2O, washed with brine, and dried over MgSO4. The solvents were
removed, and the crude product was purified by column chromatog-
raphy (silica gel, 10% Et2O/pentane) to yield the chiral ketone 1a
(63 mg, 90% yield, 97% ee) as a colorless oil.
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[10] When tetrabutylammonium fluoride in THF was used (08C, 1 h),
partial racemization of the ketone 1a was observed (86% yield,
65% ee; see the Supporting Information.
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2004, 6, 529.
Received: January 20, 2006
Published online: April 28, 2006
[12] For the use of (Ph)2CuLi in the presence of tetramethylsilyl
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b) Bis(trimethylsilyl)peroxide [(TMSO)2] was purchased from
ABCR Product List. Please refer to the warnings in the catalog.
Keywords: allylic substitution · asymmetric synthesis ·
carbonyl compounds · copper · zinc
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