Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling

Synlett

Volumn , Issue 11, 2004, Pages 1957-1960

  Davies, Stephen G ^a   Smith, Andrew D ^a   Cowley, Andrew R ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Conjugate addition; Oligomerisation; Piperidin 2 one; Three component coupling

Indexed keywords

BETA AMINO ACID; PIPERIDONE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; HYDROGENATION; OLIGOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 4544265900     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830887     Document Type: Article

References (41)

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29. The configuration of the minor diastereoisomer arising from this three-component coupling is unknown but is not identical to either diastereoisomer obtained from the stepwise [2+1] reaction manifold.
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35. A minor reaction product in the preparation of 14 and 15 was diethyl (E)-cinnamyl malonate, isolated in 19% and 15% yield (with respect to diethyl phenylallylidenemalonate), respectively, which arises from in situ conjugate reduction by lithium amide (S)-1. For selected examples of lithium amides acting as reducing agents see: (a) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. (b) Wittig, G.; Frommeld, H.-D. Chem. Ber. 1964, 97, 3541. (c) Scott, L. T.; Carlin, K. J.; Schultz, T. H. Tetrahedron Lett. 1978, 19, 4637. (d) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450. (e) Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1. (f) Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237.
36. A minor reaction product in the preparation of 14 and 15 was diethyl (E)-cinnamyl malonate, isolated in 19% and 15% yield (with respect to diethyl phenylallylidenemalonate), respectively, which arises from in situ conjugate reduction by lithium amide (S)-1. For selected examples of lithium amides acting as reducing agents see: (a) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. (b) Wittig, G.; Frommeld, H.-D. Chem. Ber. 1964, 97, 3541. (c) Scott, L. T.; Carlin, K. J.; Schultz, T. H. Tetrahedron Lett. 1978, 19, 4637. (d) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450. (e) Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1. (f) Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237.
37. A minor reaction product in the preparation of 14 and 15 was diethyl (E)-cinnamyl malonate, isolated in 19% and 15% yield (with respect to diethyl phenylallylidenemalonate), respectively, which arises from in situ conjugate reduction by lithium amide (S)-1. For selected examples of lithium amides acting as reducing agents see: (a) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. (b) Wittig, G.; Frommeld, H.-D. Chem. Ber. 1964, 97, 3541. (c) Scott, L. T.; Carlin, K. J.; Schultz, T. H. Tetrahedron Lett. 1978, 19, 4637. (d) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450. (e) Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1. (f) Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237.
38. A minor reaction product in the preparation of 14 and 15 was diethyl (E)-cinnamyl malonate, isolated in 19% and 15% yield (with respect to diethyl phenylallylidenemalonate), respectively, which arises from in situ conjugate reduction by lithium amide (S)-1. For selected examples of lithium amides acting as reducing agents see: (a) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. (b) Wittig, G.; Frommeld, H.-D. Chem. Ber. 1964, 97, 3541. (c) Scott, L. T.; Carlin, K. J.; Schultz, T. H. Tetrahedron Lett. 1978, 19, 4637. (d) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450. (e) Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1. (f) Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237.
39. A minor reaction product in the preparation of 14 and 15 was diethyl (E)-cinnamyl malonate, isolated in 19% and 15% yield (with respect to diethyl phenylallylidenemalonate), respectively, which arises from in situ conjugate reduction by lithium amide (S)-1. For selected examples of lithium amides acting as reducing agents see: (a) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. (b) Wittig, G.; Frommeld, H.-D. Chem. Ber. 1964, 97, 3541. (c) Scott, L. T.; Carlin, K. J.; Schultz, T. H. Tetrahedron Lett. 1978, 19, 4637. (d) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450. (e) Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1. (f) Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237.
40. A minor reaction product in the preparation of 14 and 15 was diethyl (E)-cinnamyl malonate, isolated in 19% and 15% yield (with respect to diethyl phenylallylidenemalonate), respectively, which arises from in situ conjugate reduction by lithium amide (S)-1. For selected examples of lithium amides acting as reducing agents see: (a) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. (b) Wittig, G.; Frommeld, H.-D. Chem. Ber. 1964, 97, 3541. (c) Scott, L. T.; Carlin, K. J.; Schultz, T. H. Tetrahedron Lett. 1978, 19, 4637. (d) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450. (e) Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1. (f) Takeda, K.; Ohnishi, Y.; Koizumi, T. Org. Lett. 1999, 1, 237.
41. 1 = 0.0253 [I>3σ(I)]. Crystallographic data (excluding structure factors) has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC240141. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: 444 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].