Stereospecific reaction of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with Grignard reagents -: Synthesis of highly enantioenriched secondary alcohols

被引：78

作者：

Beckmann, E ^{[1
]}

Desai, V ^{[1
]}

Hoppe, D ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

SYNLETT | 2004年 / 13期

关键词：

boron; asymmetric synthesis; alcohols; chirality; stereoselectivity;

D O I：

10.1055/s-2004-832835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioenriched secondary alcohols were synthesized by treatment of alpha-carbamoyloxy-2-alkenylboronates and alpha-carbamoyloxy-alkylboronates with Grignard reagents. An intermediary boronate complex was transformed stereospecifically to the corresponding secondary 2-alkenyl- and alkylboronates by migration of an introduced residue. Oxidative workup furnished the enantioenriched secondary alcohols.

引用

页码：2275 / 2280

页数：6

共 47 条

[1] Cleavage of vinyl carbon-silicon bond in γ-trimethylsilyl allylic alcohols [J].

Al-Hassan, MI ;

Miller, RB .

SYNTHETIC COMMUNICATIONS, 2001, 31 (23) :3641-3645

[2] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .30. E-PENTENYLBORONATES AND Z-PENTENYLBORONATES, REAGENTS FOR SIMPLE DIASTEREOSELECTION ON ADDITION TO ALDEHYDES [J].

ANDERSEN, MW ;

HILDEBRANDT, B ;

KOSTER, G ;

HOFFMANN, RW .

CHEMISCHE BERICHTE, 1989, 122 (09) :1777-1782

[3] Enantioselective catalytic addition of allyl organometallic reagents to aldehydes promoted by [Cr(Salen)]: the hidden role played by weak Lewis acids in metallo-Salen promoted reactions [J].

Bandini, M ;

Cozzi, PG ;

Umani-Ronchi, A .

TETRAHEDRON, 2001, 57 (05) :835-843

[4] DIPOLE-STABILIZED CARBANIONS - THE ALPHA'-LITHIATION OF PIPERIDIDES [J].

BEAK, P ;

ZAJDEL, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1010-1018

[5]

BECKMANN E, UNPUB SYNTHESIS

[6] Stereoselective reactions of acyclic allylic phosphates with organocopper reagents [J].

Belelie, JL ;

Chong, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5552-5555

[7] BETA-HYDROXYSULFOXIMINES IN THE CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE [J].

BOLM, C ;

FELDER, M .

TETRAHEDRON LETTERS, 1993, 34 (38) :6041-6044

[8] MECHANISM OF HYDRIDE ATTACK IN REDUCTION OF TRANS-1-TERT BUTYL-3-PHENYLALLY AND 1-TERT BUTYLE-3-PHENYLPROPARGL ALCOHOLS [J].

BORDEN, WT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (16) :4898-&

[9] Enantioselective reduction of ketones by borane catalysed by oxazaphospholidine oxides [J].

Chiodi, O ;

Fotiadu, F ;

Sylvestre, M ;

Buono, G .

TETRAHEDRON LETTERS, 1996, 37 (01) :39-42

[10] THE LUPIN ALKALOIDS .14. [J].

CLEMO, GR ;

RAPER, R ;

SHORT, WS .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (MAR) :663-665

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