Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes

被引：133

作者：

Patil, Nitin T. ^{[1
]}

Lutete, Leopold Mpaka ^{[1
]}

Wu, Huanyou ^{[1
]}

Pahadi, Nirmal K. ^{[1
]}

Gridnev, Ilya D. ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 11期

关键词：

D O I：

10.1021/jo0603835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd-2(dba)(3)center dot CHCl3/PhCOOH/renorphos 4 in benzene (or benzene-hexane) at 100 degrees C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.

引用

页码：4270 / 4279

页数：10

共 118 条

[1] Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes [J].

Ackermann, L ;

Bergman, RG ;

Loy, RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11956-11963

[2] A highly reactive titanium precatalyst for intramolecular hydroamination reactions [J].

Ackermann, L ;

Bergman, RG .

ORGANIC LETTERS, 2002, 4 (09) :1475-1478

[3]

[Anonymous], MODERN THEORETICAL C

[4] BAKERS-YEAST REDUCTION OF ARYLALKYL AND ARYLALKENIL GAMMA-KETO AND DELTA-KETO ACIDS [J].

AQUINO, M ;

CARDANI, S ;

FRONZA, G ;

FUGANTI, C ;

FERNANDEZ, RP ;

TAGLIANI, A .

TETRAHEDRON, 1991, 47 (37) :7887-7896

[5] PALLADIUM-CATALYZED ADDITIONS OF AMINES TO CONJUGATED DIENES - ALTERATION OF BEHAVIOR OF (TRIPHENYLPHOSPHINE)PALLADIUM CATALYSTS WITH AMINE HYDROIODIDE SALTS [J].

ARMBRUSTER, RW ;

MORGAN, MM ;

SCHMIDT, JL ;

LAU, CM ;

RILEY, RM ;

ZABROWSKI, DL ;

DIECK, HA .

ORGANOMETALLICS, 1986, 5 (02) :234-237

[6] CAPILLARY GAS-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS WITH STABLE DIPENTYL-ALPHA-CYCLODEXTRIN-DERIVATIZED, BETA-CYCLODEXTRIN-DERIVATIZED AND GAMMA-CYCLODEXTRIN-DERIVATIZED STATIONARY PHASES [J].

ARMSTRONG, DW ;

LI, WY ;

STALCUP, AM ;

SECOR, HV ;

IZAC, RR ;

SEEMAN, JI .

ANALYTICA CHIMICA ACTA, 1990, 234 (02) :365-380

[7] Intramolecular hydroamination of alkynes catalyzed by Pd(PPh3)4/triphenylphosphine under neutral conditions [J].

Bajracharya, GB ;

Huo, ZB ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4883-4886

[8] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[9] SYNTHESIS OF ALLYLIC AMINES THROUGH THE PALLADIUM-CATALYZED HYDROAMINATION OF ALLENES [J].

BESSON, L ;

GORE, J ;

GAZES, B .

TETRAHEDRON LETTERS, 1995, 36 (22) :3857-3860

[10] Quantum dynamical study of β-hydrogen transfer in two selected late-transition-metal complexes [J].

Bittner, M ;

Köppel, H .

JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (50) :11116-11126

← 1 2 3 4 5 6 7 8 9 10 →