STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .35. ADDITION OF E-CROTYLBORONATES AND Z-CROTYLBORONATES TO CHIRAL ALPHA-SUBSTITUTED ALDEHYDES

被引：44

作者：

BRINKMANN, H ^{[1
]}

HOFFMANN, RW ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,HANS MEERWEIN STR,W-3550 MARBURG,GERMANY

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 12期

关键词：

ALLYLBORATION REACTION; ASYMMETRIC INDUCTION; CALCULATIONS; FORCE-FIELD; TRANSITION-STATE MODELS;

D O I：

10.1002/cber.19901231223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direction (Cram/anti-Cram) and the extent of asymmetric induction on addition of crotylboronates to a range of chiral aldehydes was investigated. A reversal in the sense of the asymmetric induction on changing from the Z- to the E-crotylboronate was found for aldehydes having polar-alpha-substituents and for some of the nonpolar chiral aldehydes. Force-field calculations on transition-state models reproduced these results in the majority of the cases investigated despite of unaccounted short comings of the method.

引用

页码：2395 / 2401

页数：7

共 28 条

[1] A HIGHLY DIASTEREOSELECTIVE ADDITION OF (E)-CROTYLDIISOPINOCAMPHEYLBORANES AND (Z)-CROTYLDIISOPINOCAMPHEYLBORANES TO ALPHA-SUBSTITUTED ALDEHYDES
BROWN, HC
BHAT, KS
RANDAD, RS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) : 3701 - 3702
[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY
BROWN, HC
BHAT, KS
RANDAD, RS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1570 - 1576
[3] STUDIES OF AN INTRAMOLECULAR DIELS-ALDER APPROACH TO THE NARGENICINS - INVOLVEMENT OF BOATLIKE TRANSITION-STATES IN THE CYCLIZATIONS OF SUBSTITUTED 1,7,9-DECATRIEN-3-ONES
COE, JW
ROUSH, WR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) : 915 - 930
[4] A GENERAL STEREOSELECTIVE SYNTHESIS OF OLEFINS
CORNFORTH, JW
CORNFORTH, RH
MATHEW, KK
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JAN): : 112 - 127
[5] DREWES MW, 1988, THESIS U MARBURG
[6] ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125
[7] SYN/ANTI-CONFIGURATIONAL ASSIGNMENT OF SEC-BUTYLCARBINOLS BASED ON C-13-NMR SPECTRA
HILDEBRANDT, B
BRINKMANN, H
HOFFMANN, RW
[J]. CHEMISCHE BERICHTE, 1990, 123 (04) : 869 - 873
[8] Hoffman R. W., 1988, BORON CHEM, P337
[9] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .34. TOWARDS AN UNDERSTANDING OF CRAM ANTI-CRAM SELECTIVITY ON ADDITION OF CROTYLBORONATES TO ALPHA-METHYLBUTYRALDEHYDE
HOFFMANN, RW
BRINKMANN, H
FRENKING, G
[J]. CHEMISCHE BERICHTE, 1990, 123 (12) : 2387 - 2394
[10] HOFFMANN RW, 1985, CHEM SCRIPTA, V25, P53

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