Prev. Article Next Article Table of Contents

Note

Highly Diastereoselective Catalytic Meerwein−Ponndorf−Verley Reductions

Supporting Info

Jingjun Yin,* Mark A. Huffman, Karen M. Conrad, and Joseph D. Armstrong, III

Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065 jingjun_yin@merck.com

J. Org. Chem., 2006, 71 (2), pp 840–843

DOI: 10.1021/jo052121t

Publication Date (Web): December 16, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein−Ponndorf−Verley (MPV) reduction of protected α-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with α-alkoxy ketones and other compounds via Felkin−Ahn control.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue January 20, 2006
Received October 10, 2005

Recommend & Share

Related Content

A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment: Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley ReductionJournal of the American Chemical Society
- A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment: Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley Reduction
  Andrew K. Dilger, Vijay Gopalsamuthiram, and Steven D. Burke
  Journal of the American Chemical Society 2007 129 (51), pp 16273–16277
  Abstract: A three-step synthesis of a precursor to the C11−C23 segment of (−)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels−Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, ...
  Abstract | Full Text HTML | Hi-Res PDF
Recent Developments In Meerwein−Ponndorf−Verley and Related Reactions for the Reduction of Organic Functional Groups Using Aluminum, Boron, and Other Metal Reagents: A ReviewOrganic Process Research & Development
- Recent Developments In Meerwein−Ponndorf−Verley and Related Reactions for the Reduction of Organic Functional Groups Using Aluminum, Boron, and Other Metal Reagents: A Review
  Jin Soon Cha
  Organic Process Research & Development 2006 10 (5), pp 1032–1053
  Abstract | Full Text HTML | Hi-Res PDF
Catalytic Meerwein−Pondorf−Verley Reduction by Simple Aluminum ComplexesOrganic Letters
- Catalytic Meerwein−Pondorf−Verley Reduction by Simple Aluminum Complexes
  E. Joseph Campbell, Hongying Zhou, and SonBinh T. Nguyen
  Organic Letters 2001 3 (15), pp 2391–2393
  Abstract: Catalytic MPV reduction was successfully carried out using simple aluminum precatalysts. Alkylaluminum reagents were converted to a low-aggregation aluminum alkoxide that was highly active for the MPV reduction of several carbonyl substrates in high yield ...
  Abstract | Full Text HTML | Hi-Res PDF

Note

Highly Diastereoselective Catalytic Meerwein−Ponndorf−Verley Reductions

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment: Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley Reduction

Recent Developments In Meerwein−Ponndorf−Verley and Related Reactions for the Reduction of Organic Functional Groups Using Aluminum, Boron, and Other Metal Reagents: A Review

Catalytic Meerwein−Pondorf−Verley Reduction by Simple Aluminum Complexes

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES