- Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes
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The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asymmetric reductive transposition of the in situ generated allylic diazene. Acyclic 1,4-diene products bearing either alkyl- or aryl-substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios of up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in either a 1,4-syn or anti relationship from the corresponding E- or Z-crotylboronate used in the reaction. The use of β-monosubstituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.
- Jiang, Yao,Thomson, Regan J.,Schaus, Scott E.
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supporting information
p. 16631 - 16635
(2017/12/13)
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- Iodine catalyzed selective O-alkylation of alcohols with orthoesters
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In the present communication O-alkylation of a number of allylic and benzylic alcohols has been described.
- Kumar,Anjaneyulu,Joyasawal, Sipak,Pawan Chakravarthy,Naveen Kumar,Yadav
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p. 189 - 192
(2008/02/13)
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- PALLADIUM(0)-CATALYZED AZIDATION OF ALLYL ESTERS WITH TRIMETHYLSILYL AZIDE
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Palladium(0)-catalyzed reaction of allyl esters with trimethylsilyl azide gives, under anhydrous conditions, the corresponding allyl azides.
- Safi, M.,Fahrang, R.,Sinou, D.
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p. 527 - 530
(2007/10/02)
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- ELECTROCHEMICAL OXIDATION OF ORGANOSILICON COMPOUNDS I. OXIDATIVE CLEAVAGE OF CARBON-SILICON BOND IN ALLYLSILANES AND BENZYLSILANES
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Electrochemical oxidation of allylsilanes and benzylsilanes in the presence of alcohol, carboxylic acid, or water resulted in cleavage of the carbon-silicon bond and formation of the corresponding ether, ester, or alcohol, respectively.
- Yoshida, Jun-ichi,Murata, Toshiki,Isoe, Sachihiko
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p. 3373 - 3376
(2007/10/02)
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