Asymmetric Synthesis of a New Salen Type-titanium Complex as the Catalyst for Asymmetric Trimethylsilylcyanation of Aldehydes
This work describes the asymmetric synthesis of a new salen-type ligand via a Diels-Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destro...
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| Published in | Journal of the Chinese Chemical Society (Taipei) Vol. 57; no. 4A; pp. 726 - 737 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Chinese Chemical Soc
01.08.2010
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| Abstract | This work describes the asymmetric synthesis of a new salen-type ligand via a Diels-Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destroy this rigidity, and the eanatioselectivity was thereby increased to 85%ee. |
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| AbstractList | This work describes the asymmetric synthesis of a new salen-type ligand via a Diels-Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destroy this rigidity, and the eanatioselectivity was thereby increased to 85%ee. |
| Author | Chen, Chinpiao Lin, Zheng-Chang |
| Author_xml | – sequence: 1 givenname: Zheng-Chang surname: Lin fullname: Lin, Zheng-Chang organization: Natl Dong Hwa Univ, Dept Chem, Shoufeng 974, Hualien, Taiwan – sequence: 2 givenname: Chinpiao surname: Chen fullname: Chen, Chinpiao organization: Natl Dong Hwa Univ, Dept Chem, Shoufeng 974, Hualien, Taiwan |
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| CitedBy_id | crossref_primary_10_1002_ejoc_201601028 crossref_primary_10_1002_slct_201803003 crossref_primary_10_1002_jccs_201100555 crossref_primary_10_1021_acsomega_9b01682 crossref_primary_10_1002_jccs_201100474 crossref_primary_10_1021_acs_joc_8b02318 |
| Cites_doi | 10.1016/j.tetasy.2005.05.035 10.1021/ja002024b 10.1021/ol0262338 10.1055/s-2005-864831 10.1021/ol034158a 10.1002/chem.200400506 10.1021/jo0161779 10.1039/b206943c 10.1021/jo0488356 |
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| Keywords | DOUBLE-ACTIVATION METHOD Curtius rearrangement Trimethylsilylcyanation AROMATIC-ALDEHYDES HIGH OPTICAL PURITY ALPHA-ALKOXY ALDEHYDES ENANTIOSELECTIVE CYANOSILYLATION Asymmetric synthesis CHEMOENZYMATIC SYNTHESIS HYDROGEN-CYANIDE AMINO ALDEHYDES Diels-Alder reaction CHIRAL LEWIS-ACID |
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| References | Lee, PT (WOS:000231719800004) 2005; 16 Ward, DE (WOS:000172715900030) 2001; 79 MATTHEWS, BR (WOS:A1989AU42600031) 1989; 30 JACKSON, WR (WOS:A1990CU58300024) 1990; 31 Chang, TH (WOS:A1997YG42300007) 1997; 44 Chen, FX (WOS:000224357100017) 2004; 10 Monterde, MI (WOS:000083164400026) 1999; 10 Iovel, I (WOS:A1997WX80100021) 1997; 8 REETZ, MT (WOS:A1988P210900004) 1988; 29 TANAKA, K (WOS:A1990CH55800030) 1990; 55 Chang, CW (WOS:000173465800023) 2002 Wada, M (WOS:000071049800016) 1997; 8 FURUTA, K (WOS:A1986D991600034) 1986; 27 Ward, DE (WOS:000085554500016) 2000; 2 Sawada, D (WOS:000165205000004) 2000; 122 JACKSON, WR (WOS:A1990EN62200009) 1990; 43 LARROW, JF (WOS:A1994NF80700062) 1994; 59 Jiang, YZ (WOS:A1995TM38600011) 1995; 6 HAYASHI, M (WOS:A1993KT16600037) 1993; 58 Andres, JM (WOS:000167689600024) 2001; 12 Khazaei, A (WOS:000230529400017) 2005; 52 MOHAN, R (WOS:A1991GB15800014) 1991; 34 Takacs, JM (WOS:A1997XZ44200014) 1997; 8 Chou, TC (WOS:000244623400034) 2006; 53 Casas, J (WOS:000176938200036) 2002; 4 Yang, ZH (WOS:000170447000009) 2001; 12 Yang, ZH (WOS:000187222000019) 2003; 14 Ziegler, T (WOS:000089843700019) 2000; 11 NITTA, H (WOS:A1992JR86300002) 1992; 114 Laval, G (WOS:000181584100021) 2003 Fechter, MH (WOS:000173623900005) 2001; 20 Chen, FX (WOS:000181586500043) 2003; 5 Sellner, H (WOS:000090033100005) 2000; 6 Ooi, T (WOS:000166687000009) 2001; 57 Effenberger, F (WOS:A1997WJ13200020) 1997; 8 Bolm, C (WOS:000180272200005) 2003; 27 Li, Y (WOS:000225024200018) 2004; 69 Chen, FX (WOS:000228272400002) 2005 Chuang, TH (WOS:000237261100022) 2006; 53 Abiko, A (WOS:A1996UD65300007) 1996; 61 Hamashima, Y (WOS:000079363300055) 1999; 121 Liang, S (WOS:000175169000045) 2002; 67 |
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| Title | Asymmetric Synthesis of a New Salen Type-titanium Complex as the Catalyst for Asymmetric Trimethylsilylcyanation of Aldehydes |
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