Distinct advantage of the in situ generation of quaternary ammonium fluorides under phase-transfer conditions toward catalytic asymmetric synthesis

Organic Letters

Volumn 3, Issue 9, 2001, Pages 1273-1276

  Ooi, Takashi ^a   Doda, Kanae ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

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EID: 0001391862     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000382d     Document Type: Article

References (34)

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24. 21 which is obviously critical in the present system.
25. 2O (5 equiv) in THF was stirred at room temperature for 1 h, the resulting supernatant solution was transferred to another flask and treated with benzaldehyde (1.2 equiv) and 1-trimethlysiloxycyclohexene (2, 1 equiv) at -78 °C for 30 min, producing β-hydroxy ketone 3 in 85% yield with an erythro/threo ratio of 23:77.
26. 22 structurally well-defined 1a (X = Br) could enhance the rate of ion-exchange with potassium enolate of the glycine derivative initially formed at the interface and effectively extract the enolate union deep into the toluene phase with the aid of its lipophilicity, leading to the observed reactivity enhancement. In addition. 1a (X = Br) does not suffer from Hofmann elimination because of the unique N-spiro structure without β-hydrogen, which would also contribute to the high reactivity.
27. 4) slightly lowered the enantioselectivity (73% ee) in this case.
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30. Unfortunately, attempted reaction of 4 with 3-phenylpropanal under similar conditions gave rise to the aldol product in only 14% yield with an eryhro/threo ratio of 46:54, and the enantioselectivity of the erythro isomer was determined to be 46% ee. We also investigated other end silyl ethers in the aldol reaction with α-naphthaldehyde under the optimized conditions, and the following results imply the present limitation of our approach: 1-trimethylsiloxyindene [94% yield, 80% ee (erythro isomer; erythro/threo = 96:4), 1-trimethlysiloxycyclohexene (2) [80% yield, 29% ee (erythro isomer; erythro/threo = 71:29)].
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