Highly stereoselective anti SN2′ substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2111-2114

  Harrington Frost, Nicole ^a   Leuser, Helena ^a   Calaza, M Isabel ^a   Kneisel, Florian F ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; COPPER COMPLEX; ORGANOMETALLIC COMPOUND; ZINC COMPLEX;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0141630613     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034525i     Document Type: Article

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66. Although it is stated that the allyl pentafluorobenzoate (S)-(Z)-4 has 99.3% ee, it contains 0.5% of the trans isomer (S)-(E)-4. As a result, the "real" ee for the pure cis compound (S)-(Z)-4 would be 98.6% ee, so the loss of enantiomeric excess during the allylation reaction is even less important.
67. 2, pentane) afforded the desired alkene (R)-(E)-5 as a colorless liquid (88 mg, 97%, 93% ee).