Asymmetric synthesis of 1-substituted 2-azaspiro[3.3]heptanes: important motifs for modern drug discovery

被引：11

作者：

Reddy, Leleti Rajender ^{[1
]}

Waman, Yogesh ^{[1
]}

Kallure, Priya ^{[1
]}

Nalivela, Kumara Swamy ^{[1
]}

Begum, Zubeda ^{[1
]}

Divya, Thumbar ^{[1
]}

Kotturi, Sharadsrikar ^{[1
]}

机构：

[1] Piramal Discovery Solut, Route Scouting Dept, Sarkhej Bavla Highway, Ahmadabad 382213, Gujarat, India

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 35期

关键词：

TERT-BUTANESULFINYL IMINES; AMINO-ACIDS; SULFINIMINES; ANTI-2,3-DIAMINO; OPTIMIZATION; PROTOCOL;

D O I：

10.1039/c9cc00863b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly diastereoselective addition of ethyl cyclobutanecarboxylate anions to Davis-Ellman's imines is reported. Thismethodology afforded the preparation of enantiomerically and diastereomerically pure 1-substituted 2-azaspiro[3.3] heptanes. This three-step procedure proceeded efficiently (yield up to 90%) and diastereoselectively (dr values up to 98 : 2). This methodology is applicable to the synthesis of 1-substituted 2-azaspiro[3.4] octane and 1-substituted 2-azaspiro[3.5]nonane.

引用

页码：5068 / 5070

页数：3

共 31 条

[1] 1-Substituted 2-Azaspiro[3.3]heptanes: Overlooked Motifs for Drug Discovery
Kirichok, Alexander A.
Shton, Iryna
Kliachyna, Maria
Pishel, Iryna
Mykhailiuk, Pavel K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (30) : 8865 - 8869
[2] Asymmetric Synthesis of Substituted 2-Azaspiro[3.5]nonan-1-ones: An Enantioselective Synthesis of the Cholesterol Absorption Inhibitor (+) SCH 54016
J Org Chem, 23 (8341):
[3] Asymmetric synthesis of substituted 2-azaspiro[3.5]nonan-1-ones: An enantioselective synthesis of the cholesterol absorption inhibitor (+)-SCH 54016
Chen, LY
Zaks, A
Chackalamannil, S
Dugar, S
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23): : 8341 - 8343
[4] Asymmetric Synthesis 1-Substituted 2,6-Diazaspiro[3.3]heptanes through Addition of 3-Azetidinecarboxylate Anions to Davis-Ellman Imines
Reddy, Leleti Rajender
Waman, Yogesh
Nayak, Krishna
Baharooni, Kasimraza
Kotturi, Sharadsrikar
ORGANIC LETTERS, 2019, 21 (10) : 3481 - 3484
[5] Synthesis of 1-Substituted 2-Azaspiro[4.5]deca-6,9-dien-8-ones and 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones by Condensation of 2,6-Dimethylphenol with Isobutyraldehyde and Nitriles
Rozhkova, Yu. S.
Khmelevskaya, K. A.
Shklyaev, Yu. V.
Ezhikova, M. A.
Kodess, M. I.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (01) : 69 - 77
[6] Functionalized Derivatives of 2-azaspiro[3.3]heptane-1-carboxylic Acid and 7oxa-2-azaspiro[3.5] nonane-1-carboxylic Acid for Drug Design
Kirichok, Alexander A.
Yegorova, Tetyana
FRENCH-UKRAINIAN JOURNAL OF CHEMISTRY, 2023, 11 (02): : 31 - 38
[7] SYNTHESIS OF BRIDGEHEAD DERIVATIVES .2. PREPARATION OF 1-SUBSTITUTED BICYCLO[2.2.1]HEPTANES
MARTINEZ, AG
VILAR, ET
LOPEZ, JC
ALONSO, JM
HANACK, M
SUBRAMANIAN, LR
SYNTHESIS-STUTTGART, 1991, (05): : 353 - 354
[8] Synthesis of 1-substituted 2-azaspiro[4.5]deca-6,9-dien-8-ones and 2-azaspiro[4.5]deca-1,6,9-trien-8-ones by condensation of 2,6-dimethylphenol with isobutyraldehyde and nitriles
Yu. S. Rozhkova
K. A. Khmelevskaya
Yu. V. Shklyaev
M. A. Ezhikova
M. I. Kodess
Russian Journal of Organic Chemistry, 2012, 48 : 69 - 77
[9] Spirocyclohexadienones: XII. Dienone-phenol rearrangement of 1-substituted 2-azaspiro[4.5]undeca-1,6,9-trienes and their analogs
V. A. Glushkov
E. V. Rotermel’
T. F. Odegova
Yu. V. Shklyaev
Russian Journal of Organic Chemistry, 2011, 47 : 1318 - 1322
[10] Synthesis of challenging 6-functionalized 1-oxaspiro[3.3]heptanes-New scaffolds for drug discovery
Kozyriev, Yevhenii K.
Palchykov, Vitalii A.
TETRAHEDRON LETTERS, 2023, 122

← 1 2 3 4 →