Issue 35, 2008
From the journal:

Chemical Communications

Brønsted acid catalyzed regioselectiveaza-Ferrier reaction: a novel synthetic method for α-(N-Boc-2-pyrrolidinyl) aldehydes†

Eiji Tayama,*a   Seijun Otoyamaa  and  Wataru Isakaa  

* Corresponding authors

a Graduate School of Science and Technology, Niigata University, Japan
E-mail: tayama@gs.niigata-u.ac.jp
Fax: 81 25 262 7741
Tel: 81 25 262 7741

Abstract

The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)pyrrolidines (1) is shown to proceed with high (1E,3E)-stereoselectivity to afford N-Boc-2-(1,3-dienyloxy)pyrrolidines (2); the Brønsted acid catalyzed aza-Ferrier reaction of the N-Boc-2-(1,3-dienyloxy)pyrrolidines (2) provides α-(N-Boc-2-pyrrolidinyl) aldehydes (3) in excellent yields with high α-regioselectivities.

Graphical abstract: Brønsted acid catalyzed regioselectiveaza-Ferrier reaction: a novel synthetic method for α-(N-Boc-2-pyrrolidinyl) aldehydes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B806492J
Article type
Communication
Submitted
16 Apr 2008
Accepted
27 May 2008
First published
15 Jul 2008

Chem. Commun., 2008, 4216-4218

Permissions

Request permissions

Brønsted acid catalyzed regioselectiveaza-Ferrier reaction: a novel synthetic method for α-(N-Boc-2-pyrrolidinyl) aldehydes

E. Tayama, S. Otoyama and W. Isaka, Chem. Commun., 2008, 4216 DOI: 10.1039/B806492J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements