Catalytic asymmetric allylation reactions using BITIP catalysis and 2-substituted allylstannanes as surrogates for β-keto ester dianions

Organic Letters

Volumn 1, Issue 2, 1999, Pages 289-291

  Keck, Gary E ^a   Yu, Tao ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BINOL, NAPHTHOL; ESTER; NAPHTHOL DERIVATIVE; ORGANOTIN COMPOUND; OXOACID; TITANIUM; TITANIUM ISOPROPOXIDE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; CATALYSIS; ESTERS; KETO ACIDS; NAPHTHOLS; ORGANOTIN COMPOUNDS; STEREOISOMERISM; TITANIUM;

EID: 0033614865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990603j     Document Type: Article

References (23)

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9. This is a powerful disconnection; for recent examples of syntheses using such reactions, see: (a) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Prunet, J. A.; Charette, A. B.; Lautens, M. Angew. Chem., Int. Ed. 1998, 37, 2354.
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21. 1-6 The sense of asymmetric induction was also the same as previously observed: i.e., benzaldehyde affords S product using S-BINOL.
22. This is a curious result, and is clearly a kinetic phenomenon, perhaps associated with a preferred geometry for formation of the enolate anion with sodium as counterion. Use of DBU to effect this transformation affords a 9:1 mixture. After extended reaction times, the sodium hydride promoted process also affords a 9:1 mixture.
23. 4: C, 64.27; H, 7.19. Found: C, 64.18; H, 7.21.