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Recyclable chiral metathesis catalysts

A metal catalyst, a chiral technology, applied in the preparation of the catalyst, a chiral transition metal catalyst for a stereoselective olefin metathesis reaction, the preparation of the chiral catalyst, a chiral transition metal catalyst, a catalytic stereoselective olefin metathesis reaction, transition In the field of metal catalysts, it can solve problems such as instability and limited applicability, and achieve the effect of easy separation

Inactive Publication Date: 2005-08-24
BOSTON COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these catalysts are extremely sensitive to air and moisture, limiting their applicability to a range of terminal olefin-containing substrates
Furthermore, isolation of prior art chiral metathesis catalysts from the reaction product is often problematic due to the instability of the product when purified by chromatographic methods

Method used

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  • Recyclable chiral metathesis catalysts
  • Recyclable chiral metathesis catalysts
  • Recyclable chiral metathesis catalysts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 1-Bromo-2-methoxynaphthalene. Prepared according to literature methods. Majetich, G.; Hicks, R.; Reister, S., J. Org. Chem. (1997), 62, 4321-4326.

[0063]IR(NaCl): 3047(w), 2972(m), 2943(m), 2843(m), 1622(s), 1596(m), 1501(s), 1467(m), 1454(m), 14.40(w), 1353(m), 1335(m), 1271(s), 1247(w), 1219(m), 1187(m), 1173(w), 1153(w), 1064(s), 1023(m), 892(m), 840(m), 813(m), 803(s), 763(m), 743(s), 518(m).

[0064] 1 H NMR (400MHz, CDCl 3 ): δ8.19(d, J=8.6Hz, 1H), 7.75(t, J=8.5Hz, 2H), 7.53(t, J=8.2Hz, 1H), 7.36(t, J=7.9Hz, 1H ), 7.22 (d, J=9.0Hz, 1H), 3.98 (s, 3H).

[0065] 13 C NMR (100MHz, CDCl 3 ): δ153.88, 133.25, 130.94, 129.09, 128.16, 127.86, 126.24, 124.43, 113.74, 108.78, 57.17.

[0066] HRMS calculated value C 11 h 9 BrO: 235.9837. Found: 235.9838.

[0067] Analytical calculated value C 11 h 9 BrO: C, 55.72; H, 3.83. Found: C, 55.66; H, 3.82.

Embodiment 2

[0069] Methyl 1-methoxynaphthoate. Prepared according to the method described in the literature Hattori, T.; Hotta, H.; Miyano, S. Bull. Chem. Soc. Jpn. (1993), 66, 613-622.

[0070] IR(NaCl): 3058(w), 2997(w), 2948(m), 2846(w), 1725(s), 1628(m), 1597(m), 1570(m), 1504(m), 1466(m), 1445(m), 1434(m), 1373(s), 1343(s), 1279(s), 1239(s), 1214(m), 1191(m), 1153(m), 1133(s), 1084(s), 1001(m), 829(m), 802(m), 787(m), 768(s), 715(w).

[0071] 1 H NMR (400MHz, CDCl 3 ): δ8.30-8.26(m, 1H), 7.87-7.84(m, 2H), 7.62(d, J=8.6Hz, 1H), 7.61-7.54(m, 2H), 4.07(s, 3H), 3.99 (s, 3H).

[0072] 13 C NMR (100MHz, CDCl 3 ): δ166.85, 158.44, 136.93, 128.47, 128.02, 126.83, 126.68, 123.78, 123.77, 119.34, 63.56, 52.41.

[0073] HRMS calculated value C 13 h 12 o 3 : 216.0786. Measured value: 216.0787.

[0074] Analytical calculated value C 13 h 12 o 3 : C, 72.21; H, 5.59. Found: C, 72.50; H, 5.52.

Embodiment 3

[0076] 1-(-)-menthyloxy-2-naphthoic acid-(-)-menthyl ester is described in Hattori, T.; Hotta, H.; Miyano, S. Bull. Chem. Soc. Jpn. (1993) , 66, prepared by the method of 613-622.

[0077] IR(NaCl): 3058(w), 2954(s), 2956(s), 2869(m), 1719(s), 1625(w), 1598(w), 1568(w), 1502(w), 1457(m), 1387(m), 1371(m), 1342(m), 1319(m), 1277(s), 1235(s), 1215(m), 1203(m), 1181(w), 1148(s), 1137(s), 1098(m), 1081(s), 1038(w), 1007(w), 983(m), 962(m), 920(w), 823(w), 801(w), 766(m), 741(w).

[0078] 1 H NMR (400MHz, CDCl 3 ): δ8.32(d, J=8.5Hz, 1H), 7.81(d, J=7.7Hz, 1H), 7.67(d, J=8.6Hz, 1H), 7.56-7.48(m, 3H), 5.04 (td, J=10.9, 4.4Hz, 1H), 4.34(td, J=10.9, 4.2Hz, 1H), 2.67(quintetd, J=6.8, 2.2Hz, 1H), 2.21-2.16(m, 1H), 2.05(quintetd, J=7.2, 2.7Hz, 1H), 1.79-1.52(m, 7H), 1.28-0.83(m, 23H), 0.74(d, J=6.6Hz, 3H).

[0079] 13 C NMR (100MHz, CDCl 3 ):δ166.77,154.10,136.24,130.12,127.86,127.74,126.22,126.00,124.56,122.40,121.15,82.11,74.59,49.64,47.27,41.17,39.97,34.59,34.46,31.67,31.61,26....

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Abstract

The present invention relates to chiral metal catalysts for stereoselective olefin metathesis reactions, which are recyclable and reusable in such metathesis reactions. The chiral metal-based metathesis catalysts of the invention comprise multidentate optically active or racemic chiral ligands that enable their use in asymmetric synthetic processes, such as for example, in ring-opening and ring-closing metathesis reactions (ROM and RCM, respectively) of alkenes. The catalysts of the invention are organometallic complexes of multivalent metals comprising one or more chiral bidentate ligands that exhibit superior reactivity and stereoselectivity properties. The present invention also provides methods of making such catalysts and methods for utilizing them in catalyzing stereoselective olefin metathesis reactions to provide asymmetric products in relatively high enantiomeric or stereoisomeric excess.

Description

technical background [0001] Metal-catalyzed olefin metathesis reactions were used as a starting point to develop several regioselective and stereoselective methods. These methods are important steps in the chemical synthesis of complex organic compounds and polymers. In particular, these reactions are often decisive steps in the medicinal chemistry of small molecule synthesis. Organometallic catalysts, especially transition metal coordination compounds based on osmium, ruthenium or tungsten, are used for many of these organic transformation reactions. The catalytic activity of molybdenum-based chiral catalysts for asymmetric synthesis involving ring-closing metathesis reactions (RCM) of terminal olefins has been reported, see, for example, La et al. J. Am. Chem. Soc., (1998) 120, 9720. However, these catalysts are extremely sensitive to air and moisture, thus limiting their applicability to a range of terminal olefin-containing substrates. Furthermore, the isolation of prio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F11/00C07F15/00
CPCB01J31/2247B01J31/2278C07F15/0046C07F11/005C07F15/002C07F15/0073B01J2531/66B01J2531/0266B01J31/2208B01J2531/64B01J2231/543B01J31/226B01J2531/822B01J31/2273B01J31/2226B01J2531/821
Inventor 阿米尔·H.·霍维达乔希阿·范·费尔德赫伊曾史蒂文·B.·加贝尔贾森·S.·兴斯伯里
Owner BOSTON COLLEGE
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