Direct catalytic synthesis of enantiopure 5-substituted oxazolidinones from racemic terminal epoxides

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1983-1985

  Bartoli, Giuseppe ^a   Bosco, Marcella ^a   Carlone, Armando ^a   Locatelli, Manuela ^a   Melchiorre, Paolo ^a   Sambri, Letizia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; MATERIALS HANDLING; RACEMIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 19544362396     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050675c     Document Type: Article

References (23)

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18. 4) with urethane occurred with modest regioselectivity to afford a mixture of isomeric amino alcohol adducts.
19. For an evaluation of the exceptionally high selectivity of the AKR (selectivity factors exceeding 3000 for selected substrates) see ref 6 and the Supporting Information.
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21. This scenario represents an ideal case and is very rare for a kinetic resolution promoted by a chemo-catalyst. During the AKR, one enantiomer is transformed quickly and the other is unreactive, thus the reaction comes to a standstill at 50% conversion; therefore, over-resolution is not possible.
22. Kim, S. K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2004, 43, 3952. As reported, high regiocontrol for the terminal position was achieved only in the ring-opening of aliphatic epoxides with sulfonamide 6.
23. 2/THF), see the Supporting Information for details.