Catalytic asymmetric allylation reactions using BITIP catalysis and 2-substituted allylstannanes as surrogates for beta-keto ester dianions.
[formula: see text] Catalytic asymmetric allylation (CAA) reactions using the indicated allylstannane and the BITIP catalysts previously described by us give high yields and enantioselectivities in additions to aldehydes. The products are convertible to beta-keto esters by oxidative cleavage of the olefin. These reactions thus provide a useful catalytic enantioselective method for chain extension with introduction of a versatile four-carbon unit.
Keck
G E
GE
Department of Chemistry, University of Utah, Salt Lake City 84112-0850, USA. keck@chemistry.utah.edu
Yu
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D000498:Allyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D004952:Esters; D007651:Keto Acids; D009284:Naphthols / Q000737:chemistry*; D009942:Organometallic Compounds; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000498:Allyl Compounds; C406944:BINOL, naphthol; D004952:Esters; D007651:Keto Acids; D009284:Naphthols; D009942:Organometallic Compounds; D009947:Organotin Compounds; C102815:titanium isopropoxide; D014025:Titanium