New strategy for the preparation of nitrogen- and phosphorus-containing chiral polyfunctional secondary alcohols

被引：24

作者：

Lutz, C ^{[1
]}

Graf, CD ^{[1
]}

Knochel, P ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00487-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of borane-derived protecting groups for aldehydes containing pyridine and phosphine functionalities allows the performance of highly enantioselective additions of functionalized diorganizincs leading to polyfunctional chiral hydroxy-pyridines and -phosphines with excellent enantioselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10317 / 10328

页数：12

共 37 条

[1] OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS [J].

BOLM, C ;

ZEHNDER, M ;

BUR, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02) :205-207

[2] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES [J].

BOLM, C ;

EWALD, M ;

FELDER, M ;

SCHLINGLOFF, G .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1169-1190

[3]

Bolm C., 1990, Angew. Chem, V102, P206

[4] PHOSPHINE-BORANE COMPLEXES - DIRECT USE IN ASYMMETRIC CATALYSIS [J].

BRISSET, H ;

GOURDEL, Y ;

PELLON, P ;

LECORRE, M .

TETRAHEDRON LETTERS, 1993, 34 (28) :4523-4526

[5] ISOQUINOLINE-N-BORANES AS PRECURSORS TO SUBSTITUTED TETRAHYDROISOQUINOLINES [J].

BROOKS, DJ ;

DOWELL, DS ;

MINTER, DE ;

VILLARREAL, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01) :130-133

[6] SELECTIVE REDUCTIONS .46. EFFECT OF THE STERIC REQUIREMENT AT THE 2-POSITION OF APOPINENE ON CHIRAL REDUCTIONS - B-(ISO-2-ETHYLAPOPINOCAMPHEYL)-9-BORABICYCLO[3.3.1]NONANES AND B-(ISO-2-N-PROPYLAPOPINOCAMPHEYL)-9-BORABICYCLO[3.3.1]NONANES AS IMPROVED REAGENTS FOR THE CHIRAL REDUCTION OF ALPHA,BETA-ACETYLENIC KETONES AND ALPHA-KETO ESTERS [J].

BROWN, HC ;

RAMACHANDRAN, PV ;

WEISSMAN, SA ;

SWAMINATHAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6328-6333

[7] CHIRAL LIGANDS CONTAINING HETEROATOMS .8. 2-[(2S)-2-PYRROLIDINYL]PYRIDINE AS A NOVEL CATALYST IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].

CHELUCCI, G ;

CONTI, S ;

FALORNI, M ;

GIACOMELLI, G .

TETRAHEDRON, 1991, 47 (38) :8251-8258

[8] SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES [J].

IMAMOTO, T ;

OSHIKI, T ;

ONOZAWA, T ;

KUSUMOTO, T ;

SATO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5244-5252

[9] CATALYZED ASYMMETRIC REACTION OF ALDEHYDES WITH DIALKYLZINC IN THE PRESENCE OF CHIRAL PYRIDYL ALCOHOLS AS LIGANDS [J].

ISHIZAKI, M ;

FUJITA, K ;

SHIMAMOTO, M ;

HOSHINO, O .

TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :411-424

[10] LEWIS ACID COMPLEXED HETEROATOM CARBANIONS - SYNTHESIS OF SOME ALPHA-PYRIDYL ALCOHOLS [J].

KESSAR, SV ;

SINGH, P ;

SINGH, KN ;

DUTT, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (08) :570-571

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