Ethanol → (R,R)-Hydrobenzoin

HRID 1935292Notes

Reaction equation

HRID 1935292 reaction equation
C1(/C=C/C2C=CC=CC=2)C=CC=CC=1.[CH3:15][CH2:16][C@@H:17]1[CH:22]2[CH2:23][C@H:24]([C@@H:25]([O:38]C(C3C=CC(Cl)=CC=3)=O)[C:26]3C=CN=[C:32]4[C:27]=3[CH:28]=[C:29](OC)[CH:30]=[CH:31]4)N(CC2)C1.CC[OH:50]>>[C:27]1([C@@H:26]([OH:50])[C@@H:25]([C:24]2[CH:15]=[CH:16][CH:17]=[CH:22][CH:23]=2)[OH:38])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 638088trans-StilbeneHCID 14165086HCID 14165086, compound

Product 1

HCID 853019(R,R)-HydrobenzoinYield 92%

Procedure

Catalytic asymmetric dihydroxylation reaction of trans-stilbene by using LDH-osmate of the formula IIa The reaction was performed by using an identical process as in Example 9 except the cinchona alkaloid is DHQD-CLB. (R,R)-(+)-1,2-diphenyl-1,2-ethandiol of more than 98.0% of enantiomeric excess was obtained (yield 92%) [∝]D+91.32 (c 1.0, EtOH): e.e.=98.2%

Sources & evidence

ORD record
ord-c88d6540eb1544fba98d2c93fe9e0ee8
Source dataset
uspto-grants-2002_05
Patent number
US06387033B1

Reaction notes

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