Organic Letters 2002-10-31

Tandem asymmetric conjugate addition--silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications.

Oliver Knopff, Alexandre Alexakis

文献索引：Org. Lett. 4 , 3835, (2002)

摘要

[formula: see text] The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCI and NEt3. These enantiomerically enriched silyl enol ethers were submitted to four synthetic transformations to show their synthetic utility. The zinc enolates obtained from acyclic enones were found to be configurationally stable, as shown by the stereochemistry of the silyl enol ethers.

结构式	名称/CAS号	分子式	全部文献
	(S,S,S)-(+)-(3,5-二氧杂-4-磷杂环庚二烯并[2,1-a:3,4-a']二萘-4-基)二(1-苯基乙基)胺 CAS:380230-02-4	C₃₆H₃₀NO₂P
	(11bS)-N,N-双[(R)-1-苯基乙基]-联萘并[2,1-d:1',2'-f][1,3,2]二氧膦杂-4-胺 CAS:497883-22-4	C₃₆H₃₀NO₂P

Copper-catalyzed enantioselective conjugate addition of dial...
2005-09-02
[J. Org. Chem. 70 , 7451, (2005)]

[Synlett , 1375, (2001)]

[Org. Biomol. Chem. 4 , 1278, (2006)]

Marcovic´, D.; Hartwig, J. F.
[J. Am. Chem. Soc. 129 , (2007)]

Tandem asymmetric conjugate addition--silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications.

摘要

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