Efficient synthesis of a key intermediate of neurokinin receptor antagonists using a bifunctional asymmetric catalyst

被引：17

作者：

Takamura, M ^{[1
]}

Yabu, K

Nishi, T

Yanagisawa, H

Kanai, M

Shibasaki, M

机构：

[1] Sankyo Co Ltd, Med Chem Res Labs, Shinagawa Ku, Tokyo 1408710, Japan

[2] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

SYNLETT | 2003年 / 03期

关键词：

D O I：

10.1055/s-2003-37123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report herein an efficient synthetic method for the preparation of 2-[(2R)-arylmorpholin-2-yl]ethanol, a key intermediate of neurokinin receptor antagonists. Catalytic asymmetric cyanosilylation of ketone 3 using titanium complex 4 was employed to introduce the required stereochemistry.

引用

页码：353 / 356

页数：4

共 9 条

[1] CLAY RJ, 1993, SYNTHESIS-STUTTGART, P290
[2] Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning
Hamashima, Y
Kanai, M
Shibasaki, M
[J]. TETRAHEDRON LETTERS, 2001, 42 (04) : 691 - 694
[3] Catalytic enantioselective cyanosilylation of ketones
Hamashima, Y
Kanai, M
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) : 7412 - 7413
[4] Practical synthesis of chiral ligands for catalytic enantioselective cyanosilylation of ketones
Masumoto, S
Yabu, K
Kanai, M
Shibasaki, M
[J]. TETRAHEDRON LETTERS, 2002, 43 (16) : 2919 - 2922
[5] An efficient synthesis of enantiomerically pure 2-[(2R)-arylmorpholin-2-yl]ethanols, key intermediates of tachykinin receptor antagonist
Nishi, T
Ishibashi, K
Nakajima, R
Iio, Y
Fukazawa, T
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (18) : 3251 - 3262
[6] NISHI T, 1996, Patent No. 776893
[7] REGOLI D, 1994, PHARMACOL REV, V46, P551
[8] A versatile method for the preparation of 2,2-disubstituted morpholine analogues
Takemoto, T
Iio, Y
Nishi, T
[J]. TETRAHEDRON LETTERS, 2000, 41 (11) : 1785 - 1788
[9] Switching enantiofacial selectivities using one chiral source:: Catalytic enantioselective synthesis of the key intermediate for (20S)-camptothecin family by (S)-selective cyanosilylation of ketones
Yabu, K
Masumoto, S
Yamasaki, S
Hamashima, Y
Kanai, M
Du, W
Curran, DP
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) : 9908 - 9909

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