Regiodivergent Ring Opening of Chiral Aziridines
Kinetic resolution of strained three-membered rings has proven broadly useful for the generation of enantiopure organic intermediates. Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good...
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| Veröffentlicht in: | Science (American Association for the Advancement of Science) 2009-12, Vol.326 (5960), p.1662-1662 |
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| container_issue | 5960 |
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| container_title | Science (American Association for the Advancement of Science) |
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| creator | Wu, Bin Parquette, Jon R RajanBabu, T.V |
| description | Kinetic resolution of strained three-membered rings has proven broadly useful for the generation of enantiopure organic intermediates. Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good yield with exceptionally high enantioselectivity. Specifically, the dimeric yttrium salen catalyst accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic attack at the primary position of one enantiomer and the secondary position of the other. Both rate and selectivity are highly sensitive to the catalyst structure. |
| doi_str_mv | 10.1126/science.1180739 |
| format | Article |
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Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good yield with exceptionally high enantioselectivity. Specifically, the dimeric yttrium salen catalyst accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic attack at the primary position of one enantiomer and the secondary position of the other. 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Herein we demonstrate a complementary approach whereby a single catalyst transforms a racemic mixture of aziridines to a pair of regioisomeric products, each in good yield with exceptionally high enantioselectivity. Specifically, the dimeric yttrium salen catalyst accelerates the ring opening of aliphatic aziridines by trimethylsilylazide, inducing nucleophilic attack at the primary position of one enantiomer and the secondary position of the other. Both rate and selectivity are highly sensitive to the catalyst structure.</description><subject>Azides</subject><subject>Aziridines</subject><subject>Brevia</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical compounds</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Enantiomers</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Kinetics</subject><subject>Materials</subject><subject>Molecular structure</subject><subject>Organic chemistry</subject><subject>Reagents</subject><subject>Theory of reactions, general kinetics. Catalysis. 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| ispartof | Science (American Association for the Advancement of Science), 2009-12, Vol.326 (5960), p.1662-1662 |
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| source | American Association for the Advancement of Science; Jstor Complete Legacy |
| subjects | Azides Aziridines Brevia Catalysis Catalysts Chemical compounds Chemical reactions Chemistry Enantiomers Exact sciences and technology General and physical chemistry Kinetics Materials Molecular structure Organic chemistry Reagents Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Regiodivergent Ring Opening of Chiral Aziridines |
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