PMID- 29600546
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20180613
LR  - 20180613
IS  - 1521-3765 (Electronic)
IS  - 0947-6539 (Linking)
VI  - 24
IP  - 32
DP  - 2018 Jun 7
TI  - Cooperative Catalysis with Coupled Chiral Induction in 1,3-Dipolar Cycloadditions 
      of Azomethine Ylides.
PG  - 8092-8097
LID - 10.1002/chem.201801433 [doi]
AB  - 1,3-Dipolar cycloadditions (1,3-DC) between imino esters (as precursors of 
      N-metallated azomethine ylides) and pi-deficient alkenes are promoted by 
      cooperative asymmetric Lewis acid/Bronsted base catalysis. The components of 
      these catalytic pairs are silver salts derived from enantiopure commercially 
      available BINOL-based phosphoric acids and Cinchona alkaloids. Chiral phosphoric 
      silver(I) salts promote HOMO raising of in situ formed 1,3-dipoles, whereas 
      protonated cinchona alkaloids generate a LUMO lowering for the dipolarophiles 
      resulting in a global acceleration of the 1,3-DC. The best results were obtained 
      with BINOL-derived silver phosphate and hydrocinchonine. Matching between both 
      cooperative metallo- and organocatalyst results in an enhanced enantiomeric 
      excess, superior to that reached by both separate components. NOESY experiments 
      and DFT calculations are compatible with a non-covalent interaction (hydrogen 
      bond) between both catalysts, which results in close contacts and mutually 
      coupled chiral environments.
CI  - (c) 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Cayuelas, Alberto
AU  - Cayuelas A
AD  - Departamento de Quimica Organica, Universidad de Alicante., Ctra. Alicante-San 
      Vicente s/n, 03080, Alicante, Spain.
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
FAU - Larranaga, Olatz
AU  - Larranaga O
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
AD  - Departamento de Quimica Organica I, Facultad de Quimica, Universidad del Pais 
      Vasco/Euskal Herriko Unibertsitatea UPV/EHU, P. K. 1072, E-20018, San Sebastian, 
      Spain.
FAU - Selva, Veronica
AU  - Selva V
AD  - Departamento de Quimica Organica, Universidad de Alicante., Ctra. Alicante-San 
      Vicente s/n, 03080, Alicante, Spain.
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
AD  - Institute of Organic Synthesis, Universidad de Alicante, Spain.
FAU - Najera, Carmen
AU  - Najera C
AUID- ORCID: 0000-0003-0063-5527
AD  - Departamento de Quimica Organica, Universidad de Alicante., Ctra. Alicante-San 
      Vicente s/n, 03080, Alicante, Spain.
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
FAU - Akiyama, Takahiko
AU  - Akiyama T
AD  - Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, 
      Toshima-ku, Tokyo, 171-8588, Japan.
FAU - Sansano, Jose M
AU  - Sansano JM
AUID- ORCID: 0000-0002-5536-2717
AD  - Departamento de Quimica Organica, Universidad de Alicante., Ctra. Alicante-San 
      Vicente s/n, 03080, Alicante, Spain.
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
AD  - Institute of Organic Synthesis, Universidad de Alicante, Spain.
FAU - de Cozar, Abel
AU  - de Cozar A
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
AD  - Departamento de Quimica Organica I, Facultad de Quimica, Universidad del Pais 
      Vasco/Euskal Herriko Unibertsitatea UPV/EHU, P. K. 1072, E-20018, San Sebastian, 
      Spain.
AD  - IKERBASQUE, Basque Foundation for Science, 48011, Bilbao, Spain.
FAU - Miranda, Jose I
AU  - Miranda JI
AD  - SGIker NMR Facility, Universidad del Pais Vasco, Spain.
FAU - Cossio, Fernando P
AU  - Cossio FP
AUID- ORCID: 0000-0001-8668-536X
AD  - Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Spain.
AD  - Departamento de Quimica Organica I, Facultad de Quimica, Universidad del Pais 
      Vasco/Euskal Herriko Unibertsitatea UPV/EHU, P. K. 1072, E-20018, San Sebastian, 
      Spain.
LA  - eng
PT  - Journal Article
DEP - 20180515
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
OTO - NOTNLM
OT  - asymmetric catalysis
OT  - cooperative catalysis
OT  - cycloadditions
OT  - density functional calculations
OT  - enantioselective synthesis
EDAT- 2018/03/31 06:00
MHDA- 2018/03/31 06:01
CRDT- 2018/03/31 06:00
PHST- 2018/03/20 00:00 [received]
PHST- 2018/03/31 06:00 [pubmed]
PHST- 2018/03/31 06:01 [medline]
PHST- 2018/03/31 06:00 [entrez]
AID - 10.1002/chem.201801433 [doi]
PST - ppublish
SO  - Chemistry. 2018 Jun 7;24(32):8092-8097. doi: 10.1002/chem.201801433. Epub 2018 
      May 15.