Synthesis, resolution, and applications of 2,2′-bis(diphenylphosphino)-3,3′-binaphtho[2,1-b]furan

被引:68
作者
Andersen, NG [1 ]
Parvez, M [1 ]
Keay, BA [1 ]
机构
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
关键词
D O I
10.1021/ol006238+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short five-step synthesis of (+/-)-2,2'-bis(diphenylphosphino)-3,3'-binaphtho[2,1-b](BINAPFu, 1) starting from 2-naphthoxyacetic acid is reported. The resolution of BINAPFu 1 was possible using our newly developed resolution procedure for phosphines wherein (1 S)-camphorsulfonyl azide was used to prepare the bisphosphinimine of BINAPFu via the Staundinger reaction. BINAPFu consistently outperformed BINAP in an asymmetric Heck reaction between 2,3 dihydrofuran and phenyl triflate.
引用
收藏
页码:2817 / 2820
页数:4
相关论文
共 32 条
[1]   THE CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .15. P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE DONOR PROPERTIES OF HETEROARYLPHOSPHINES TOWARDS SELENIUM AND PLATINUM(II) [J].
ALLEN, DW ;
TAYLOR, BF .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1982, (01) :51-54
[2]   Comparative reactivity of palladium(0) complexes generated in situ in mixtures of triphenylphosphine or tri-2-furylphosphine and Pd(dba)2 [J].
Amatore, C ;
Jutand, A ;
Meyer, G ;
Atmani, H ;
Khalil, F ;
Chahdi, FO .
ORGANOMETALLICS, 1998, 17 (14) :2958-2964
[3]   A novel resolution procedure for the preparation of P-stereogenic phosphine oxides [J].
Andersen, NG ;
Ramsden, PD ;
Che, DQ ;
Parvez, M ;
Keay, BA .
ORGANIC LETTERS, 1999, 1 (12) :2009-2011
[4]  
ANTOGNAZZA P, Patent No. 9601831
[5]   New class of chiral diphosphine ligands for highly efficient transition metal-catalyzed stereoselective reactions: The bis(diphenylphosphino) five-membered biheteroaryls [J].
Benincori, T ;
Brenna, E ;
Sannicolo, F ;
Trimarco, L ;
Antognazza, P ;
Cesarotti, E ;
Demartin, F ;
Pilati, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6244-6251
[6]   Synthesis and resolution of 2,2'-bis-diphenylphosphino[3,3']biindolyl; A new atropisomeric ligand for transition metal catalysis [J].
Berens, U ;
Brown, JM ;
Long, J ;
Selke, R .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :285-292
[7]   (R)- and (S)-6,6'-dimethyl- and 6,6'-dimethoxy-2,2'-diiodo-1,1'-biphenyls: Versatile intermediates for the synthesis of atropisomeric diphosphine ligands [J].
Cereghetti, M ;
Arnold, W ;
Broger, EA ;
Rageot, A .
TETRAHEDRON LETTERS, 1996, 37 (30) :5347-5350
[8]  
CRISTOFOLI WA, 1994, SYNLETT, P625
[9]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[10]   EFFICIENT SYNTHESIS OF (R)-(6,6'-DIFLUOROBIPHENYL-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE) AND (S)-(6,6'-DIFLUOROBIPHENYL-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE) - ELECTRON-POOR BIPHENYL-TYPE LIGANDS FOR TRANSITION-METAL CATALYSTS [J].
JENDRALLA, H ;
LI, CH ;
PAULUS, E .
TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1297-1320