Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic ammonium salts and their conversion to optically active dialkyl diselenides

被引：13

作者：

Murai, Toshiaki ^{[1
]}

Monzaki, Masaki ^{[1
]}

Shibahara, Fumitoshi ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan

来源：

CHEMISTRY LETTERS | 2007年 / 36卷 / 07期

关键词：

D O I：

10.1246/cl.2007.852

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically pure phosphoroselenoyl chloride reacted with Et3N in the presence of H2O to give a phosphoroselenoic tertiary ammonium salt. Formation of the salt was confirmed by X-ray molecular structure analysis. The quaternary ammonium salt was prepared by reacting phosphoroselenoic acid O-2-silylethyl ester with Bu4NF. The alkylation of tertiary ammonium salt with racemic alkyl halides gave phosphoroselenoic acid Se-esters as diastereomeric mixtures. The cleavage of Se-esters with Bu4NF gave optically active dialkyl diselenides.

引用

页码：852 / 853

页数：2

共 50 条

[1] Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites
Murai, Toshiaki
Inaji, Shinsuke
Morishita, Ken
Shibahara, Fumitoshi
Tokunaga, Makoto
Obora, Yasushi
Tsuji, Yasushi
[J]. CHEMISTRY LETTERS, 2006, 35 (12) : 1424 - 1425
[2] 1,1′-Binaphthyl-2,2′-diyl benzylphosphoramidate
Gowda, Ravikumar R.
Ramkumar, Venkatachalam
Chakraborty, Debashis
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3310 - U1895
[3] Triethylammonium 1,1′-binaphthyl-2,2′-diyl phosphate
Gowda, Ravikumar R.
Ramkumar, Venkatachalam
Chakraborty, Debashis
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1625 - U1037
[4] ASYMMETRIC-SYNTHESIS OF ACIDS BY THE PALLADIUM-CATALYZED HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL OR (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE
ALPER, H
HAMEL, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) : 2803 - 2804
[5] ENANTIOMERIC (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL AND (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE - (DINAPHTHO[2,1-D-1',2'-F][1,3,2]DIOXAPHOSPHEPIN, 4-HYDROXY-1,1'-BINAPHTHYL-2,2'-DIYL, 4-OXIDE)
JACQUES, J
FOUQUEY, C
[J]. ORGANIC SYNTHESES, 1989, 67 : 1 - 12
[6] Racemic and Optically Active 1,1′-Binaphthyl-2,2′-diyl Sulfite: Synthesis, Crystal Structure, and Ring-Opening Reactions with Selected Nucleophiles
Drabowicz, Jozef
Krasowska, Dorota
Marciniak, Bernard
Rozycka-Sokolowska, Ewa
[J]. HETEROATOM CHEMISTRY, 2011, 22 (3-4) : 562 - 570
[7] DIASTEREOSELECTIVE SYNTHESIS OF 1,1'-BINAPHTHYL-2,2'-DIOL
WANG, M
LIU, SZ
LIU, J
HU, BF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22): : 7364 - 7365
[8] Chiral recognition of 1,1′-binaphthyl-2,2′-diyl hydrogenphosphate using fluorescence anisotropy
Xu, Yafei
McCarroll, Matthew E.
[J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2007, 187 (2-3) : 139 - 145
[9] CONVENIENT SYNTHESIS OF 1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID
OI, S
MATSUNAGA, K
HATTORI, T
MIYANO, S
[J]. SYNTHESIS-STUTTGART, 1993, (09): : 895 - 898
[10] catena-Poly[[trimethyltin(IV)]-μ-(1,1′-binaphthyl-2,2′-diyl phosphonato)]
Wu, Jianjun
Zhang, Rufen
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : M63 - U687

← 1 2 3 4 5 →