DOI: 10.1002/anie.200461286. Readily Available Biaryl P,N Ligands for Asymmetric Catalysis

Readily Available Biaryl P,N Ligands for Asymmetric Catalysis

10.1002/anie.200461286

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

KnÃ¶pfel, T. F., Aschwanden, P., Ichikawa, T., Watanabe, T., & Carreira, E. M. (2004). Readily Available Biaryl P,N Ligands for Asymmetric Catalysis. Angewandte Chemie International Edition, 43(44), 5971â5973. Portico.

Authors 5

Thomas F. Knöpfel (first)
Patrick Aschwanden (additional)
Takashi Ichikawa (additional)
Takumi Watanabe (additional)
Erick M. Carreira (additional)

References 36 Referenced 363

{'key': 'e_1_2_2_1_2', 'volume-title': 'Comprehensive Asymmetric Catalysis', 'year': '1999'} / Comprehensive Asymmetric Catalysis (1999)
10.1002/adsc.200303138
10.1021/ar9900865
10.1016/j.tet.2003.09.066
Quinap: 1‐(2‐diphenylphosphino‐1‐naphthyl)isoquinoline.
10.1002/(SICI)1521-3765(19990401)5:4<1320::AID-CHEM1320>3.0.CO;2-#
10.1021/om0010767
10.1002/ange.200352578
10.1002/anie.200352578
10.1021/ja035851w
10.1021/ja036558z
We suggest the acronym pinap in analogy to quinap where “pi” refers to phthalazine.
10.1016/S0957-4166(00)80183-4
10.1021/op034007n
50 mg (P)‐ or (M)‐quinap costs € 143 at STREM.
10.1021/jo034510y
Depending on the scale different separation procedures were applied. Typically on >2 g scale either3 aor5 awas selectively crystallized from the mixture (see Supporting Information for details) and the residue was purified by flash chromatography. On a smaller scale the diastereomers were separated by flash chromatography; for example 1.21 g of a mixture of3 a/3 bwas separated by flash chromatography to give3 a(595 mg) and3 b(501 mg; 91 % mass recovery).
CCDC‐243850 (3 a) and CCDC‐243851 (5 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre 12 Union Road Cambridge CB2 1EZ UK; fax: (+44) 1223‐336‐033; or deposit@ccdc.cam.ac.uk).
10.1021/ja00191a049
10.1039/c39930001673
10.1002/ange.19951070820
10.1002/anie.199509311
Ligand3 bgave slightly lower enantioselectivities (89 %eein the hydroboration of styrene). The complexes with ligands5 aand5 bgave lower enantioselectivities and yields.
10.1021/ja025969x
Ligand3 bgave slightly lower enantioselectivities (93 %eefor R=CN). The complexes with ligands5 aand5 bgave lower enantioselectivities and yields.
10.1021/ja993838z
10.1021/ja016378u
10.1021/ja993074n
10.1021/ol017022q
10.1021/ja035311z
10.1021/jo01041a005
Ligands3 aand3 bgave comparable results (for R=iPr and R′=Ph;3 a: 92 %ee(R) and3 b: 94 %ee(S)).

Dates

Type	When
Created	20 years, 9 months ago (Nov. 12, 2004, 6:16 a.m.)
Deposited	1 year, 10 months ago (Oct. 11, 2023, 7:22 a.m.)
Indexed	2 hours, 10 minutes ago (Sept. 3, 2025, 6:24 a.m.)
Issued	20 years, 9 months ago (Nov. 10, 2004)
Published	20 years, 9 months ago (Nov. 10, 2004)
Published Online	20 years, 9 months ago (Nov. 10, 2004)
Published Print	20 years, 9 months ago (Nov. 12, 2004)

Funders 0

None

BibTeX

@article{Kn_pfel_2004, title={Readily Available Biaryl P,N Ligands for Asymmetric Catalysis}, volume={43}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200461286}, DOI={10.1002/anie.200461286}, number={44}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Knöpfel, Thomas F. and Aschwanden, Patrick and Ichikawa, Takashi and Watanabe, Takumi and Carreira, Erick M.}, year={2004}, month=nov, pages={5971–5973} }

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