A Novel BF3*OEt2-Catalyzed Annulation of N-Cbz-α-Amino Aldehides with Allyltrimethylsilane. Highly Stereoselective Synthesis of Cis-2,3,5-Trisubstituted Pyrrolidines

DOI: 10.1021/jo00087a003

Source and publish data:

Journal of Organic Chemistry p. 1958 - 1960 (1994)

Update date:2022-08-05

Topics:

Authors:

Kiyooka, Syun-ichi

Shiomi, Yasuhiro

Kira, Haruhide

Kaneko, Yuichi

Tanimori, Shinji

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

Article abstract of DOI:10.1021/jo00087a003

In the presence of BF3*OEt2 (0.2 molar equiv), the reactions (-10 deg C, CH2Cl2) of N-Cbz-α-amino aldehydes with allyltrimethylsilane produced pyrrolidines in good yields (70-80percent), with high all-cis stereoselectivity at the C-2, C-3, and C-5 positio

Full text of DOI:10.1021/jo00087a003

Products guided by the article

Product name:((1S,2S)-2-Hydroxy-1-isopropyl-pent-4-enyl)-carbamic acid benzyl ester

Cas No:123411-90-5

R&D Labs maybe for 123411-90-5

Guangzhou Chemical Reagent Factory

Contact:+86-20-8435 9820 or 8435 7345

Address:Southern Guangzhou, Guangdong, China
HANGZHOU ZHONGCHANG SCIENTIFIC CO.,LTD

Contact:+86-571-88932183

Address:Hangzhou
Changzhou Kingyo Chemical Corporation Ltd.

website:http://www.kingyochem.com

Contact:+86-519-85105717

Address:19# Wuqing North Road, Changzhou , Jiangsu, China
Puyang Huicheng Electronic Material Co., Ltd

website:http://huichengchem.weba.testwebsite.cn/index_en.html

Contact:+86-393-8910800

Address:West Section Shengli Road, Puyang457000, China
Dongying J&M Chemical Co., Ltd,

Contact:546-8551108

Address:Room 1219, Zisheng Mansion, Zibo Road, Dongying, Shandong, China

Relevant to this article

Chiral Primary Amine-Squaramide Catalyzed Highly Enantioselective Michael Addition of Isobutyraldehyde to Nitroolefins

Doi:10.1055/s-0036-1588090
(2017)
Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties

Doi:10.1016/j.dyepig.2010.01.001
(2010)
Development of a practical and sustainable strategy for the synthesis of ST1535 by an iron-catalyzed Kumada cross-coupling reaction

Doi:10.1016/j.tetlet.2014.01.030
(2014)
A new method for the stereoselective construction of angular methyl group of fuzed cyclic ethers

Doi:10.1016/j.tetlet.2010.05.109
(2010)
Synthesis and evaluation of α-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials

Doi:10.1021/jm100211e
(2010)
Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur

Doi:10.1039/c8cc09190k
(2019)

Article Doi