Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines

Journal of the American Chemical Society

Volumn 134, Issue 9, 2012, Pages 4011-4014

  Kim, Haejin ^a   Rhee, Young Ho ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOISOMERIZATIONS; STEREOSELECTIVE SYNTHESIS; SYNTHETIC STRATEGIES;

AMINES; STEREOCHEMISTRY; STEREOSELECTIVITY;

CATALYSIS;

ACETAL DERIVATIVE; ALKOXYALLENE; ALLENE DERIVATIVE; AMINE; PALLADIUM; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOISOMERIZATION; ISOMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

ACETALS; ALKADIENES; ALKYNES; AMINES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; PIPERIDINES; STEREOISOMERISM;

EID: 84863230128     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2116298     Document Type: Article

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47. All other enol ethers produced from the Au(I)-catalyzed cycloisomerization were converted into the corresponding piperidin-4-ones in comparable yield. For detailed data, see the SI.
48. The terminal alkyne derived from cyclohexyl N,O-acetal 6a and 6b (Table 1) showed poor conversion in the gold-catalyzed cycloisomerization.