scholarly journals A CONVENIENT METHOD FOR THE PREPARATION OF ENOL ACETATES OF α-KETO ESTERS BY THE ALKYLATION OF CYANOHYDRIN SILYL ETHERS DERIVED FROM GLYOXYLIC ESTERS WITH BENZYL AND ALLYL HALIDES

1983 ◽  
Vol 12 (7) ◽  
pp. 985-988 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Takeshi Oriyama ◽  
Masahiro Murakami
Keyword(s):  
Convenient Method ◽  
Silyl Ethers ◽  
Keto Esters ◽  
Allyl Halides ◽  
Enol Acetates

Chemistry of the Podocarpaceae. XLVIII. Photo-sensitized oxidations of unsaturated ring-c aromatic diterpenoids

1974 ◽  
Vol 27 (9) ◽  
pp. 2001 ◽  
Author(s):  
RC Cambie ◽  
RC Hayward
Keyword(s):  
Sodium Borohydride ◽  
Convenient Method ◽  
Lithium Aluminium ◽  
Enol Acetates ◽  
High Yields ◽  
General Method

Photo-sensitized oxidation of the 6,7-dehydro ring-c aromatic diterpenoids (5), (8) and (38) affords high yields of the corresponding 5-ene-7-ones (62), (63) and (69). Similar oxygenation of 13-methoxy- totara-6,8,11,13-triene (21) gives a hydroperoxide (74) which undergoes a facile rearrangement to a naphthyl derivative (80) in the presence of acid. Photo-sensitized oxidation of the enol acetates derived from the 7-oxo diterpenoids, however, provides a general method for preparation of the corresponding 5-ene-7-one. Reduction of the enone (62) with lithium aluminium hydridealuminium chloride gives a mixture of the 5,8,11,13-tetraene (66) and the 6,8,11,13-tetraene (9) while reduction with sodium borohydride and treatment of the resulting alcohols (61) and (67) with acid gives a mixture of the tetraenes (5) and (68). Photo-oxygenation of the latter mixture provides a convenient method for isolating the tetraene (68). Similar reductions of 13-methoxytotara-5,8,11,13-tetraen-7-one (76) have been examined and products from the action of m-chloroperbenzoic acid on the enol acetates (19), (20) and (7) are reported.

In-MEDIATED ALLYLATION OF α-KETO ESTERS WITH ALLYL HALIDES*

2001 ◽  
Vol 31 (20) ◽  
pp. 3189-3196 ◽  
Author(s):  
Phil Ho Lee ◽  
Kooyeon Lee ◽  
Sukbok Chang
Keyword(s):  
Keto Esters ◽  
Allyl Halides

ChemInform Abstract: In-Mediated Allylation of α-Keto Esters with Allyl Halides.

ChemInform ◽  
2010 ◽  
Vol 33 (4) ◽  
pp. no-no
Author(s):  
Phil Ho Lee ◽  
Kooyeon Lee ◽  
Sukbok Chang
Keyword(s):  
Keto Esters ◽  
Allyl Halides
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