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Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)

Hofstra, Julie L. and DeLano, Travis J. and Reisman, Sarah E. (2020) Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole). Organic Syntheses, 97 . pp. 172-188. ISSN 2333-3553. PMCID PMC8294164. doi:10.15227/orgsyn.097.0172.

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A. Bis((3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)methane (3) . An oven-dried 2-L three-necked, round-bottomed flask equipped with a 6.5 cm × 2.0 cm Teflon-coated elliptical stir bar is fitted with a thermometer, a reflux condenser and a rubber septum. The system is connected to a continuous nitrogen flow and then charged with (1R,2S)-(+)-cis-1-amino-2-indanol (1, 22.2 g, 149 mmol, 2.1 equiv), diethyl malonimidate dihydrochloride (2, 16.4 g, 71 mmol, 1 equiv), and 1 L of dichloromethane (Note 2). The system is heated to 45 °C (internal temperature 43 °C) under an atmosphere of nitrogen in an oil bath for 18 h, stirring at 600 rpm. Reaction progress is monitored by ¹H NMR (Note 3) (Figure 1).

Item Type:Article
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URLURL TypeDescription CentralArticle
Hofstra, Julie L.0000-0001-9558-4317
DeLano, Travis J.0000-0002-2052-611X
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2020 Organic Syntheses, Inc. Published on the Web 8/20/2020. Checked by Sergio Cuesta-Galisteo, Jorge A. González, and Cristina Nevado.
PubMed Central ID:PMC8294164
Record Number:CaltechAUTHORS:20201109-125642953
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:106513
Deposited By: Tony Diaz
Deposited On:09 Nov 2020 21:38
Last Modified:16 Nov 2021 18:54

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