α-Hydroxyalkyl heterocycles via chiral allylic boronates: Pd-catalyzed borylation leading to a formal enantioselective isomerization of allylic ether and amine

Journal of the American Chemical Society

Volumn 131, Issue 28, 2009, Pages 9612-9613

  Lessard, Stéphanie ^a   Peng, Feng ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ALLYLIC ETHERS; BORONATE; BORYLATION; CHEMICAL EQUATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE PREPARATION; HETEROCYCLES; ONE POT PROCESS; TRIFLATES;

ALDEHYDES; AMINES; ENANTIOSELECTIVITY; ETHERS; ISOMERIZATION; ISOMERS; PALLADIUM; STEREOSELECTIVITY;

ELECTRON TRANSITIONS;

ALDEHYDE; AMINE; BORONIC ACID DERIVATIVE; ETHER DERIVATIVE; PALLADIUM; PIPERIDINE DERIVATIVE; PYRAN DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; CYCLOADDITION; ENANTIOSELECTIVITY; ISOMERIZATION; STEREOCHEMISTRY;

ALKANES; AMINES; BORONIC ACIDS; CATALYSIS; ETHERS; HETEROCYCLIC COMPOUNDS; HYDROGEN-ION CONCENTRATION; ISOMERISM; PALLADIUM; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 67650445840     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903946f     Document Type: Article

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16. See details and additional results in the Supporting Information.
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18. 10 Values for all products are similar within analytical error: it is known that pyranyl allylic boronates similar to 3 (cf. eq 1) do not suffer erosion of optical purity in the allylboration process (ref 3b). As in the allylboration of eq 1 (ref 3b), only one diastereomer was identified.
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