2-Ene-1,4-diols by dimerization of terminal epoxides using hindered lithium amides

被引：40

作者：

Hodgson, DM ^{[1
]}

Bray, CD ^{[1
]}

Kindon, ND ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 12期

关键词：

D O I：

10.1021/OL050402h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of hindered lithium amides with readily available (enantiopure) terminal epoxides gives 2-ene-1,4-diols via carbenoid dimerization of the corresponding ct-lithiated epoxides. D-Mannitol and D-iditol were synthesized using this method in three steps from (S)-tritylglycidyl ether.

引用

页码：2305 / 2308

页数：4

共 35 条

[1] Base-induced heterochiral dimerization of an oxiranyl carbaldimine:: Stereoselective synthesis of a highly functionalized aziridine [J].

Alickmann, D ;

Fröhlich, R ;

Wurthwein, EU .

ORGANIC LETTERS, 2001, 3 (10) :1527-1530

[2] A straightforward synthesis of (-)-phaseolinic acid [J].

Amador, M ;

Ariza, X ;

Garcia, J ;

Ortiz, J .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8172-8175

[3] Stereodivergent approach to β-hydroxy α-amino acids from C2-symmetrical alk-2-yne-1,4-diols [J].

Amador, M ;

Ariza, X ;

Garcia, J ;

Sevilla, S .

ORGANIC LETTERS, 2002, 4 (25) :4511-4514

[4]

[Anonymous], CHEM ORGANOLITHIUM C, DOI DOI 10.1002/047002111X.CH18

[5]

Ariza X, 2004, SYNTHESIS-STUTTGART, P128

[6]

Ariza X, 2001, SYNLETT, P120

[7] Oxazaborolidine-catalysed reduction of alk-2-ene-1,4diones.: A convenient access to chiral 1,4-diols [J].

Bach, J ;

Berenguer, R ;

Garcia, J ;

López, M ;

Manzanal, J ;

Vilarrasa, J .

TETRAHEDRON, 1998, 54 (49) :14947-14962

[8] NEW CHIRAL PHOSPHOLANES - SYNTHESIS, CHARACTERIZATION, AND USE IN ASYMMETRIC HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

HARLOW, RL .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :569-592

[9] Stereospecific synthesis of optically active phenylpropylene oxides [J].

Capriati, V ;

Florio, S ;

Luisi, R ;

Nuzzo, I .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3330-3335

[10] Oxiranyl anion-mediated synthesis of highly enantiomerically enriched styrene oxide derivatives [J].

Capriati, V ;

Florio, S ;

Luisi, R ;

Salomone, A .

ORGANIC LETTERS, 2002, 4 (14) :2445-2448

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