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Substrate |
Equiv. of cuprate |
Conditions |
Product |
Yield(%) |
---|---|---|---|---|
1.20 |
THF/Et2O room temp. 4 hr |
71a |
||
1.50 |
THF, 31° 18 hr |
67b |
||
1.10 |
THF/Et2O 1.1 eq. BF3 −78°, 1 hr |
98b |
||
1.25 |
THF/Et2O 0°, 1 hr |
90a |
||
aIsolated yield of chromatographically pure material. |
||||
bBy quantitative GC analysis. |
Appendix
Compounds Referenced (Chemical Abstracts Registry Number)
petroleum ether
hexanes
brine
D-glyceraldehyde acetonide
(vinyl)2CuLi
(vinyl)Cu(CN)Li
Me(2-thienyl)Cu(CN)Li2
MeLi/Me2Cu(CN)Li2
(vinylic)MeCu(CN)Li2
MeLi/Me(2-thienyl)Cu(CN)Li2
(vinylic)(2-Th)Cu(CN)Li2
ethanol (64-17-5)
ethyl acetate (141-78-6)
ether (60-29-7)
ammonium chloride (12125-02-9)
sodium sulfate (7757-82-6)
copper(I) cyanide (544-92-3)
Benzophenone (119-61-9)
sodium (13966-32-0)
ammonium hydroxide (1336-21-6)
2-Pentanol (6032-29-7)
Thiophene (110-02-1)
benzyl bromide (100-39-0)
butyllithium (109-72-8)
Tetrahydrofuran, THF (109-99-9)
sodium hydride (7646-69-7)
calcium hydride (7789-78-8)
argon (7440-37-1)
vinyllithium (917-57-7)
phosphomolybdic acid (51429-74-4)
1,10-phenanthroline (66-71-7)
1-Benzyloxy-4-penten-2-ol, 4-Penten-2-ol, 1-(phenylmethoxy)- (58931-16-1)
Benzyl 2,3-epoxypropyl ether, (±)-benzyl 2,3-epoxypropyl ether (2930-05-4)
glycidol (556-52-5)
tetrabutylammonium iodide (311-28-4)
mannitol (69-65-8)
(R)/(S)-2,3-O-isopropylidene glyceraldehyde (15186-48-8)
(S)-benzyl 2,3-epoxypropyl ether (16495-13-9)