REVERSAL OF FACIAL SELECTIVITY IN THE KINETIC RESOLUTION OF OLEFIN VIA ASYMMETRIC DIHYDROXYLATION (AD) REACTION - SYNTHESIS OF OPTICALLY-ACTIVE (-)-MINTLACTONE AND (-ISOMINTLACTONE BY AD REACTION FROM INTRINSICALLY DISFAVOURED DIASTEREOFACE OF ALKENE())

Authors
LOHRAY BB NANDANAN E BHUSHAN V
Citation
Bb. Lohray et al., REVERSAL OF FACIAL SELECTIVITY IN THE KINETIC RESOLUTION OF OLEFIN VIA ASYMMETRIC DIHYDROXYLATION (AD) REACTION - SYNTHESIS OF OPTICALLY-ACTIVE (-)-MINTLACTONE AND (-ISOMINTLACTONE BY AD REACTION FROM INTRINSICALLY DISFAVOURED DIASTEREOFACE OF ALKENE()), Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 36(3), 1997, pp. 226-231
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
36
Issue
3
Year of publication
1997
Pages
226 - 231
Database
ISI
SICI code
0376-4699(1997)36:3<226:ROFSIT>2.0.ZU;2-S
Abstract
Reversal of diastereofacial selectivity in the kinetic resolution of 4 -methyl-1-(carbethoxymethylene)cyclohexane 6 has been observed during asymmetric dihydroxylation reaction using different chiral auxiliaries . The AD reaction of 6 proceeds from a favoured diastereoface when DHQ D(2)-TP or DHQD-CLB are used, whereas unfavoured diasterofacial select ion is observed when DHQD(2)-PHAL is used as chiral auxiliary. Similar ly, AD reaction of ethyl alpha-(4-methylcyclohex-1-ene)propionate 5 pr oceeds via unfavoured diasteroface; resulting in axial dihydroxylation , to afford (-)-mintlactone 1 and (+)-isomintlactone 2.