Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls.
The (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls and unsymmetrically substituted furans lead to syn regioselectivity when the furan has a 2-Me or 2-COOR substituent, while anti regioselectivity is obtained with a 3-Me or 3-COOR group. DFT calculations are performed to explain the selectivities. The reactivities and regioselectivities are consistent with the ambiphilic reactivity of amino-oxyallyls with furans.
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
Andrew G
AG
Lohse
Elizabeth H
EH
Krenske
Jennifer E
JE
Antoline
K N
KN
Houk
Richard P
RP
Hsung
D000498:Allyl Compounds / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D023303:Oxazolidinones / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D005663:Furans; D023303:Oxazolidinones; D010100:Oxygen; C039281:furan