Solid phase synthesis of alkenes using the Horner-Wadsworth-Emmons reaction and monitoring by gel phase P-31 NMR

被引：74

作者：

Johnson, CR

Zhang, BR

机构：

[1] Arris Pharmaceutical Corp., South San Francisco, CA 94080, 385 Oyster Point Blvd.

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 51期

关键词：

D O I：

10.1016/0040-4039(95)02017-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphonoacetamide eaters bound to solid supported peptides or peptide synthesis supports are active as Horner-Wadsworth-Emmons (HWE) reagents with a variety of aldehydes. HWE reagents can be attached to the solid support via the amide or phosphono eater. Mild basic conditions, triethylamine and Li salts, with excess aldehyde give high conversions to alkenes.

引用

页码：9253 / 9256

页数：4

共 17 条

[1] CARBON-CARBON BOND-FORMING METHODS ON SOLID SUPPORT - UTILIZATION OF KENNER SAFETY-CATCH LINKER
BACKES, BJ
ELLMAN, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) : 11171 - 11172
[2] C-13 NMR RELAXATION-TIMES OF A TRIPEPTIDE METHYL-ESTER AND ITS POLYMER-BOUND ANALOGS
BAYER, E
ALBERT, K
WILLISCH, H
RAPP, W
HEMMASI, B
[J]. MACROMOLECULES, 1990, 23 (07) : 1937 - 1940
[3] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
BLANCHETTE, MA
CHOY, W
DAVIS, JT
ESSENFELD, AP
MASAMUNE, S
ROUSH, WR
SAKAI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
[4] CAMPA C, 1986, AN QUIM C-ORG BIOQ, V82, P51
[5] PHOSPHONATE ESTER SYNTHESIS USING A MODIFIED MITSUNOBU CONDENSATION
CAMPBELL, DA
BERMAK, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) : 658 - 660
[6] CAMPS F, 1971, TETRAHEDRON LETT, V20, P1715
[7] ANALOGOUS ORGANIC-SYNTHESIS OF SMALL-COMPOUND LIBRARIES - VALIDATION OF COMBINATORIAL CHEMISTRY IN SMALL-MOLECULE SYNTHESIS
CHEN, CX
RANDALL, LAA
MILLER, RB
JONES, AD
KURTH, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2661 - 2662
[8] HEITZ W, 1972, ANGEW CHEM INT EDIT, P298
[9] FORMATION OF C-C BOND IN SOLID-PHASE SYNTHESIS USING THE HECK REACTION
HIROSHIGE, M
HAUSKE, JR
ZHOU, P
[J]. TETRAHEDRON LETTERS, 1995, 36 (26) : 4567 - 4570
[10] STUDIES ON POLYNUCLEOTIDES .52. USE OF 2 4 6-TRIISOPROPYLBENZENESULFONYL CHLORIDE FOR SYNTHESIS OF INTERNUCLEOTIDE BONDS
LOHRMANN, R
KHORANA, HG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (04) : 829 - +

← 1 2 →