SYNTHETIC METHODS .16. STERIC COURSE OF THE REDUCTION OF KETOACETAL ESTERS WITH ALKALI-METALS IN LIQUID-AMMONIA

被引：4

作者：

JAISLI, F

STERNBACH, D

SHIBUYA, M

ESCHENMOSER, A

机构：

[1] SWISS FED INST TECHNOL,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND

[2] TOKUSHIMA UNIV,FAC PHARMACEUT SCI,TOKUSHIMA 770,JAPAN

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1979年 / 18卷 / 08期

关键词：

D O I：

10.1002/anie.197906371

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereochemistry of the reduction of keto groups such as in 1 by alkali metals is influenced by neighboring oxygen functions. Compounds 1. R1, R2H, CO2Me, give 2 and 3 in th ratio 1:2.5–3. This unexpected finding is explained in terms of stabilization of the axial alkoxide corresponding to 3 by a Li bridge. Na+ and K + are too large for bridge formation; they give mainly 2. (Figure Presented.) Copyright © 1979 by Verlag Chemie, GmbH, Germany

引用

页码：637 / 638

页数：2

共 11 条

[1] THE STEREOCHEMISTRY OF CYCLOHEXANE DERIVATIVES
BARTON, DHR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (MAR): : 1027 - 1040
[2] THE STEREOSPECIFICITY OF CARBANION REDUCTION PROCESSES
BARTON, DHR
ROBINSON, CH
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1954, (SEP): : 3045 - 3051
[3] THE CONFORMATION OF THE STEROID NUCLEUS
BARTON, DHR
[J]. EXPERIENTIA, 1950, 6 (08): : 316 - 320
[4] C-13 MAGNETIC-RESONANCE - UPFIELD SHIFTS CAUSED BY NITROGEN, OXYGEN, AND FLUORINE-ATOMS LOCATED AT LAMBDA POSITION AND ANTI-PERIPLANAR TO NUCLEUS OBSERVED
ELIEL, EL
BAILEY, WF
KOPP, LD
WILLER, RL
GRANT, DM
BERTRAND, R
CHRISTENSEN, KA
DALLING, DK
DUCH, MW
WENKERT, E
SCHELL, FM
COCHRAN, DW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (02) : 322 - 330
[5] METAL-AMMONIA REDUCTION OF KETONES
HUFFMAN, JW
CHARLES, JT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (23) : 6486 - &
[6] MCMURRY JE, 1978, TETRAHEDRON LETT, P1633
[7] PROCTER G, UNPUBLISHED
[8] SHIBUYA M, 1979, ANGEW CHEM INT EDIT, V18, P636
[9] Shibuya M., 1979, ANGEW CHEM, V91, P672
[10] SYNTHETIC METHODS .14. FRAGMENTATIONAL APPROACH TO MACROLIDES - (5-E, 8-Z)-6-METHYL-5,8-UNDECADIEN-11-OLIDE
STERNBACH, D
SHIBUYA, M
JAISLI, F
BONETTI, M
ESCHENMOSER, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (08): : 634 - 636

← 1 2 →