5747-07-9Relevant articles and documents
Regio- and stereochemical studies on the nitroso-diels-alder reaction with 1,2-disubstituted dienes
Galvani, Gilles,Lett, Robert,Kouklovsky, Cyrille
, p. 15604 - 15614 (2013)
The regioselectivity of the nitroso-Diels-Alder reaction between unsymmetrical acyclic dienes and Boc-nitroso (Boc=tert-butoxycarbonyl) reagent or the Wightman chiral chloronitroso reagents has been studied. With the Boc-nitroso reagent, the selectivity is a consequence of steric effects at the C1-position in the diene and electronic effects at the C2-position in the diene. The combination of an unprotected hydroxyethyl side chain at C1 and an electron-withdrawing group at C2 allows complete regioselectivity in favour of the proximal isomer. The same isomer was obtained exclusively with the chiral nitroso reagent with high enantioselectivities. A model based on steric effects is proposed. Get selective! A combination of steric and electronic effects allows the design of 1,2-disubstituted dienes for highly regioselective nitroso-Diels-Alder reactions with either Boc-nitroso reagent or a chiral chloronitroso reagent. Enantiomerically enriched functionalized cycloadducts could be obtained by asymmetric and regioselective cycloadditions (see scheme; Boc=tert-butoxycarbonyl, TBS=tert-butyldimethylsilyl, Piv=pivaloyl). Copyright
Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
Adamson, Nathan J.,Hull, Ethan,Malcolmson, Steven J.
supporting information, p. 7180 - 7183 (2017/06/05)
We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.
Substituted fused bicyclic amines as modulators of chemokine receptor activity
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Page/Page column 21-22, (2010/02/13)
The present application describes modulators of CCR3 of formula (Ia) and (Ib): or pharmaceutically acceptable salt forms thereof, wherein Z, R1, R2, R3, R4, R5, R5′, R6, a, b, c, d, and u are as defined herein. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis using said modulators are disclosed.