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TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature

Posted on Sep 25, 2012

Bruce H. Lipshutz,* Subir Ghorai, Alexander R. Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, and Arkady Krasovskiy
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
Ricky D. Gaston and Robert C. Gadwood*
Kalexsyn, Inc., 4502 Campus Drive, Kalamazoo, Michigan 49008, United States

ABSTRACT: An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic R-tocopherol, MPEG- 750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several “name” reactions, including Heck, Suzuki-Miyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C-H activations, and olefin metathesis reactions. Physical data in the form of DLS and cryo-TEM measurements suggest that particle size and shape are key elements in achieving high levels of conversion and, hence, good isolated yields of products. This new amphiphile will soon be commercially available.

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Practical Synthesis of 3-Oxa-6-azabicyclo[3.1.1]heptane Hydrotosylate; a Novel Morpholine-Based Building Block

Posted on Sep 25, 2012

Synthesis 2012, 44, 2859

Authors: Dan Walker, Brian Eklov, Matthew Bedore

Abstract

Bridged bicyclic morpholines are important building blocks in medicinal chemistry research. The bicyclic morpholine 3-oxa-6-azabicylo[3.1.1]heptane (3a) is of particular interest as a morpholine isostere because it is achiral and shows similar lipophilicity to that of morpholine, based on the cLogP of a derived analogue. The first synthesis of morpholine 3a (tosylate salt) is described; the seven-step sequence begins with inexpensive starting materials and uses straightforward chemistry.

Key words

isosteres – bicyclic compounds – heterocycles – cyclization – medicinal chemistry

Supporting Information

for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.

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Two Kalamazoo businessmen named Entrepreneurs of the Year by Ernst & Young

Posted on Jan 23, 2012

By Alex Nixon | Kalamazoo Gazette

KALAMAZOO — Kalexsyn Inc. co-founders David Zimmermann and Robert Gadwood 
have been named Entrepreneurs of the Year by Ernst & Young.

Zimmermann and Gadwood, who formed Kalexsyn in 2003 after Pfizer Inc. purchased Pharmacia Corp., received the award in the technology category for the Michigan and Northwest Ohio region, according to a press release from the company.

Zimmermann is Kalexsyn’s CEO and Gadwood is the company’s president and chief scientific officer.

The award, “which recognizes outstanding entrepreneurs who are building and leading dynamic, growing businesses,” according to the release, was presented at an event in Dearborn on June 10.

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