Chiral N,O-Ligand/[Cu(OAc)2]-Catalyzed Asymmetric Construction of 4-Aminopyrrolidine Derivatives by 1,3-Dipolar Cycloaddition of Azomethine Ylides with α-Phthalimidoacrylates
A protocol to access useful 4‐aminopyrrolidine‐2,4‐dicarboxylate derivatives has been developed. A variety of chiral N,O‐ligands derived from 2,3‐dihydroimidazo[1,2‐a]pyridine motifs have been evaluated in the asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates. React...
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| Published in | Chemistry : a European journal Vol. 21; no. 29; pp. 10457 - 10465 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
13.07.2015
WILEY‐VCH Verlag |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0947-6539 1521-3765 |
| DOI | 10.1002/chem.201500966 |
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| Abstract | A protocol to access useful 4‐aminopyrrolidine‐2,4‐dicarboxylate derivatives has been developed. A variety of chiral N,O‐ligands derived from 2,3‐dihydroimidazo[1,2‐a]pyridine motifs have been evaluated in the asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates. Reactions catalyzed by copper in combination with ligand 7‐Cl‐DHIPOH provided the highest level of stereoselectivity for the 1,3‐dipolar cycloaddition reaction. The reaction tolerates both β‐substituted and β‐unsubstituted α‐phthalimidoacrylate as dipolarophiles, affording the corresponding quaternary 4‐aminopyrrolidine cycloadducts with excellent diastereo‐ (>98:2 d.r.) and enantioselectivities (up to 97 % ee). Removal of the phthalimido protecting group can be accomplished by a simple NaBH4 reduction. Theoretical calculations employing DFT methods show this cycloaddition reaction is likely to proceed through a stepwise mechanism and the stereochemistry was also theoretically rationalized.
N,O means yes: Catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates catalyzed by a new chiral N,O‐ligand/[Cu(OAc)2] system has been developed. The reaction tolerates both β‐substituted and β‐unsubstituted α‐phthalimidoacrylate as dipolarophiles. Theoretical calculations show this cycloaddition reaction is likely to proceed through a stepwise mechanism. |
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| AbstractList | A protocol to access useful 4-aminopyrrolidine-2,4-dicarboxylate derivatives has been developed. A variety of chiral N,O-ligands derived from 2,3-dihydroimidazo[1,2-a]pyridine motifs have been evaluated in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-phthalimidoacrylates. Reactions catalyzed by copper in combination with ligand 7-Cl-DHIPOH provided the highest level of stereoselectivity for the 1,3-dipolar cycloaddition reaction. The reaction tolerates both β-substituted and β-unsubstituted α-phthalimidoacrylate as dipolarophiles, affording the corresponding quaternary 4-aminopyrrolidine cycloadducts with excellent diastereo- (>98:2 d.r.) and enantioselectivities (up to 97 % ee). Removal of the phthalimido protecting group can be accomplished by a simple NaBH4 reduction. Theoretical calculations employing DFT methods show this cycloaddition reaction is likely to proceed through a stepwise mechanism and the stereochemistry was also theoretically rationalized. A protocol to access useful 4‐aminopyrrolidine‐2,4‐dicarboxylate derivatives has been developed. A variety of chiral N,O‐ligands derived from 2,3‐dihydroimidazo[1,2‐a]pyridine motifs have been evaluated in the asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates. Reactions catalyzed by copper in combination with ligand 7‐Cl‐DHIPOH provided the highest level of stereoselectivity for the 1,3‐dipolar cycloaddition reaction. The reaction tolerates both β‐substituted and β‐unsubstituted α‐phthalimidoacrylate as dipolarophiles, affording the corresponding quaternary 4‐aminopyrrolidine cycloadducts with excellent diastereo‐ (>98:2 d.r.) and enantioselectivities (up to 97 % ee). Removal of the phthalimido protecting group can be accomplished by a simple NaBH4 reduction. Theoretical calculations employing DFT methods show this cycloaddition reaction is likely to proceed through a stepwise mechanism and the stereochemistry was also theoretically rationalized. N,O means yes: Catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates catalyzed by a new chiral N,O‐ligand/[Cu(OAc)2] system has been developed. The reaction tolerates both β‐substituted and β‐unsubstituted α‐phthalimidoacrylate as dipolarophiles. Theoretical calculations show this cycloaddition reaction is likely to proceed through a stepwise mechanism. A protocol to access useful 4‐aminopyrrolidine‐2,4‐dicarboxylate derivatives has been developed. A variety of chiral N,O‐ligands derived from 2,3‐dihydroimidazo[1,2‐a]pyridine motifs have been evaluated in the asymmetric 1,3‐dipolar cycloaddition of azomethine ylides to α‐phthalimidoacrylates. Reactions catalyzed by copper in combination with ligand 7‐Cl‐DHIPOH provided the highest level of stereoselectivity for the 1,3‐dipolar cycloaddition reaction. The reaction tolerates both β‐substituted and β‐unsubstituted α‐phthalimidoacrylate as dipolarophiles, affording the corresponding quaternary 4‐aminopyrrolidine cycloadducts with excellent diastereo‐ (>98:2 d.r.) and enantioselectivities (up to 97 % ee ). Removal of the phthalimido protecting group can be accomplished by a simple NaBH 4 reduction. Theoretical calculations employing DFT methods show this cycloaddition reaction is likely to proceed through a stepwise mechanism and the stereochemistry was also theoretically rationalized. |
| Author | Fossey, John S. Wang, Zheng Yu, Xingxin Deng, Wei-Ping Liu, Yang-Zi Tian, Bo-Xue Payne, Daniel T. Yang, Wu-Lin |
| Author_xml | – sequence: 1 givenname: Zheng surname: Wang fullname: Wang, Zheng organization: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China) – sequence: 2 givenname: Xingxin surname: Yu fullname: Yu, Xingxin email: xxyu@ecust.edu.cn organization: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China) – sequence: 3 givenname: Bo-Xue surname: Tian fullname: Tian, Bo-Xue organization: Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, CA 94158 (USA) – sequence: 4 givenname: Daniel T. surname: Payne fullname: Payne, Daniel T. organization: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, B15 2TT (UK) – sequence: 5 givenname: Wu-Lin surname: Yang fullname: Yang, Wu-Lin organization: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China) – sequence: 6 givenname: Yang-Zi surname: Liu fullname: Liu, Yang-Zi organization: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China) – sequence: 7 givenname: John S. surname: Fossey fullname: Fossey, John S. organization: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, B15 2TT (UK) – sequence: 8 givenname: Wei-Ping surname: Deng fullname: Deng, Wei-Ping email: weiping_deng@ecust.edu.cn organization: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (P.R. China) |
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| Copyright | 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Keywords | density functional calculations ligands copper asymmetric synthesis cycloaddition |
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| Snippet | A protocol to access useful 4‐aminopyrrolidine‐2,4‐dicarboxylate derivatives has been developed. A variety of chiral N,O‐ligands derived from... A protocol to access useful 4-aminopyrrolidine-2,4-dicarboxylate derivatives has been developed. A variety of chiral N,O-ligands derived from... |
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| SubjectTerms | asymmetric synthesis copper cycloaddition density functional calculations ligands |
| Title | Chiral N,O-Ligand/[Cu(OAc)2]-Catalyzed Asymmetric Construction of 4-Aminopyrrolidine Derivatives by 1,3-Dipolar Cycloaddition of Azomethine Ylides with α-Phthalimidoacrylates |
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