Journal
ORGANIC LETTERS
Volume 12, Issue 22, Pages 5298-5301Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102352w
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Funding
- National Natural Science Foundation of China [20802044, 21021001]
- National Basic Research Program of China (973 Program) [2010CB833200]
- RFDP [200806101091]
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A facile and highly stereoselective retro-[1,4] Brook rearrangement of 3-silyl allyloxysilanes has been discovered. While basic hydrolysis of the formed (Z)-3,3-bissilyl lithium enolates provides 3,3-bissilyl carbonyl compounds efficiently, trapping the species with various electrophiles including alkyl halides leads to the exclusive O-substituted (2)-3,3-bissilyl enol derivatives that can undergo a Sakurai reaction with aldehyde to produce the synthetically useful 1,2-diol diastereoselectively.
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