Chemoenzymatic synthesis of the trans-dihydrodiol isomers of monosubstituted benzenes via anti-benzene dioxides.
Enantiopure cis-2,3-dihydrodiols, available from dioxygenase-catalysed cis-dihydroxylation of monosubstituted benzene substrates, have been used as synthetic precursors of the corresponding trans-3,4-dihydrodiols. The six-step chemoenzymatic route from cis-dihydrodiol precursors, involving acetonide, tetraol, dibromodiacetate and diepoxide intermediates, and substitution of vinyl bromide and iodide atoms, has been used in the synthesis of ten trans-dihydrododiol derivatives of substituted benzenes. The general applicability of the method has been demonstrated by its use in the synthesis of both enantiomers of the trans-1,2-and 3,4-dihydrodiol derivatives of toluene.
Boyd
Derek R
DR
School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast BT9 5AG, UK.
Sharma
Narain D
ND
Llamas
Nuria M
NM
O'Dowd
Colin R
CR
Allen
Christopher C R
CC
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001555:Benzene Derivatives; D009281:Naphthalenes; C507866:trans-1,2-dihydro-1,2-naphthalenediol