Stereoselective azide cycloaddition to chiral cyclopentanone enamines

DOI: 10.1016/S0957-4166(97)00239-5

Source and publish data:

Tetrahedron Asymmetry p. 2261 - 2266 (1997)

Update date:2022-08-03

Topics:

Authors:

Fioravanti, Stefania

Pellacani, Lucio

Ricci, Damiano

Tardella, Paolo A.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0957-4166(97)00239-5

The enamine derived from cyclopentanone and (2R,5R)-2,5-bis(methoxymethyl )pyrrolidine added ethyl N-mesylazidoformimidate [N₃C(OEt)NMs] and ethyl azidoformate (N₃CO₂Et) with high asymmetric induction (>95%), while the corresponding cyclohexanone enamine gave ring contraction products. With the same azides the cyclopentanone enamine, prepared from (S)-2-(methoxymethyl)pyrrolidine gave N-substituted α-amino cyclopentanones in moderate enantiomeric excess.

Full text of DOI:10.1016/S0957-4166(97)00239-5

Products guided by the article

Product name:(2R,5R)-1-Cyclohex-1-enyl-2,5-bis-methoxymethyl-pyrrolidine

Cas No:194607-35-7

R&D Labs maybe for 194607-35-7

Tianjin Crest Pharmaceutical R&D Co., Ltd. （Tianjin Yao Technology Development Co., Ltd.）(expird)

Contact:+86-22-66211386

Address:Building B5-405, No, 80 4th Avenue, TEDA, Tianjin, China P.R. 300457
Suzhou Chiral Pharmaceuticals Co., Ltd.

Contact:86-0512-63197058

Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
Beijing Ribio Biotech Co.,Ltd

Contact:86-10-62664360

Address:Building 10,No.18 AnNingZhuang East Road, GuangHua Pioneer Park,HaiDian District, BeiJing China
Jinan Finer Chemical Co., Ltd

website:https://www.finerchem.com

Contact:+86-531-88989536

Address:New Material Industrial Park, Jinan City, China
Rugao Jinling Chemical Co., Ltd.(expird)

Contact:0086-513-68005586

Address:Lianluo new village huangshi town Rugao city Jiangsu Province.

Relevant to this article

Doi:10.1016/S0040-4020(01)96318-5
(1968)
Reductive diallylation of natural amino acids with triallylborane. The first synthesis of chiral 1,1-diallyl-2-amino alcohols and their cyclization into optically active pyrrolidines

Doi:10.1016/S0040-4039(97)01402-0
(1997)
Tripod ligands containing a mixed P/N/S donor set: Synthesis and coordination chemistry

Doi:10.1002/cber.19971300917
(1997)
112. Novel heterospirocyclic 3-amino-2H-azirines as synthons for heterocyclic α-amino acids)

Doi:10.1002/hlca.19970800515
(1997)
Polyethers with phosphate pendant groups by monomer activated anionic ring opening polymerization: Syntheses, characterization and their lithium-ion conductivities

Doi:10.1016/j.polymer.2013.12.005
(2014)
Reaction of alkynes with Rh₄(CO)₁₂. A mid-infrared vibrational and kinetic study of (μ₄-η²-alkyne) Rh₄(CO)₈(μ-CO)₂

Doi:10.1021/om0510019
(2006)

Article Doi