(S,S)-Duthaler-Hafner试剂（140462-73-3）

(R,R)-Duthaler-Hafner试剂 (132068-98-5)

此两种试剂都已商业化。

利用Duthaler-Hafner试剂和烯丙基格氏试剂对醛进行对映选择性烯丙基化反应生成手性烯丙醇的反应。

反应实例

1(S)-1-Phenyl-3-buten-1-ol (4). 3 in THF (5.3 mL, 0.8 M, 4.25 mmol) was added slowly (10 min) at0 C under Ar to a solution of (R,R)-2 (3.06 g, 5 mmol) in Et2O (60 mL). After 1.5 h stirring at 0 C, the mixture was cooled to -78 C and PhCHO (403 mg, 3.8 mmol) in Et2O (5 mL) was added over 5 min.

After 3 h stirring at -74 C, the mixture was quenched with 45% NH4F (20 mL) and after separation of 1.68 g of ligand and chromatography on silica gel (DCM:hexane:Et2O 4:4:1), 521 mg of (S)-4 (93%, 95% ee) was obtained.

【Hafner A, J Am Chem Soc, 1992, 114, 2321】

    相关文献

1 Duthaler RO Helv Chim Acta 1990 73 353

2 Duthaler RO, Hafner A Pure Appl Chem 1990 62 631

3 Hafner A, Duthaler RO Eur Pat Appl Ep 387,1991 114 112718h

4 Hafner A J Am Chem Soc 1992 114 2321

5 Duthaler RO, Hafner A Chem Rev 1992 92 827

6 Duthaler RO, Hafner A lnorg Chem Acta 1994 222 95

7 Zellner A Synlett 2001 1016

8 Leighton JL Angew Chem 2003 115 976

9 Mulzer J Angew Chem Int 2009 48 6032

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 133-134.