Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine

被引：150

作者：

Chen, G ^{[1
]}

Tokunaga, N ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 11期

关键词：

D O I：

10.1021/ol0507367

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acaC)(C2H4)(2) and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones in over 99% ee. This asymmetric reaction was applied to the synthesis of (R)-tolterodine.

引用

页码：2285 / 2288

页数：4

共 56 条

[21] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions
Hayashi, T
Yamasaki, K
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2829 - 2844
[22] Hayashi T, 2002, ORG SYNTH, V79, P84
[23] Iguchi Y, 2003, SYNLETT, P1040
[24] Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds:: Large accelerating effects of bases and ligands
Itooka, R
Iguchi, Y
Miyaura, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) : 6000 - 6004
[25] Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-addition of arylboronic acids to cycloalkenones
Kuriyama, M
Nagai, K
Yamada, K
Miwa, Y
Taga, T
Tomioka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) : 8932 - 8939
[26] Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-addition of arylboronic acids to cycloalkenones
Kuriyama, M
Tomioka, K
[J]. TETRAHEDRON LETTERS, 2001, 42 (05) : 921 - 923
[27] General strategy toward the tetrahydronaphthalene skeleton. An expedient total synthesis of sertraline
Lautens, M
Rovis, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) : 5246 - 5247
[28] Asymmetric addition of aryl boron reagents to enones with rhodium dicyclophane imidazolium carbene catalysis
Ma, YD
Song, C
Ma, CQ
Sun, ZJ
Chai, Q
Andrus, MB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (47) : 5871 - 5874
[29] Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to α,β-unsaturated sulfones
Mauleón, P
Carretero, JC
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3195 - 3198
[30] Rhodium catalysed tandem conjugate addition-protonation: an enantioselective synthesis of 2-substituted succinic esters
Moss, RJ
Wadsworth, KJ
Chapman, CJ
Frost, CG
[J]. CHEMICAL COMMUNICATIONS, 2004, (17) : 1984 - 1985

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