Hydride → HCID 54032019, compound

HRID 2372101Notes

Reaction equation

HRID 2372101 reaction equation
[H-].[B].[Al].[CH2:4]([O:11][CH2:12][C:13]#[C:14][CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Pd]>[CH2:4]([O:11][CH2:12][CH:13]=[CH:14][CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 166653HydrideHCID 5359268AluminumHCID 5462311BoronHCID 19905844HCID 19905844, compound2×

Product 1

HCID 54032019HCID 54032019, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Next, a hydride of boron or aluminum or palladium catalyst is allowed to act on 5-benzyloxy-1,1,1-trifluoro-3-pentyne-2-ol (compound (3)) to obtain 5-benzyloxy-1,1,1-trifluoro-3-pentene-2-ol (E)-(5) or (Z)-(5). This is acetylated or isobutylated and then thereon is allowed lipases or lipases-producing microorganism to act to obtain optically active (R)-5-benzyloxy-1,1,1-trifluoro-3-pentene-2-ol [(R)-(E)-5] or [(R)-(Z)-5] and optically active (S)-2-acetoxy (or butoxy)-5-benzyloxy-1,1,1-trifluoro-3-pentene [(S)-(E)-6 or (S)-(Z)-6].

Sources & evidence

ORD record
ord-1af45bae1da7456fa98e34ea411244e4
Source dataset
uspto-grants-1992_03
Patent number
US05097075

Reaction notes

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