Catalytic, asymmetric Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2481-2484

  Nakamura, Yoshitaka ^a   Matsubara, Ryosuke ^a   Kiyohara, Hiroshi ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBAMIC ACID DERIVATIVE; COPPER COMPLEX; DIAMINE DERIVATIVE; ESTER; GLYCINE DERIVATIVE; NITROGEN; POLYMER; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DEPROTECTION REACTION; ENANTIOSELECTIVITY; MANNICH REACTION;

EID: 0141630824     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034717d     Document Type: Article

References (29)

1. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
2. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
3. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
4. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
5. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
6. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
7. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
8. For catalytic enantioselective Mannich-type Reactions of α-imino esters, see: (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. (c) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drurry, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (d) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995. (e) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (f) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507. (g) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1843. (h) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338. To the best of our knowledge, there has been no example of catalytic enantioselective Mannich-type reactions of N-carbamate-protected α-imino esters.
9. Only a few successful examples of catalytic enantioselective reactions of imines bearing readily removable N-carbamates have been reported so far. For Friedel-Crafts-type reactions of N-carbamate-protected α-imino esters, see: (a) Sabby, S.; Bayon, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352. For Mannich-type reactions of N-Boc-imines derived from aromatic aldehydes, see: (b) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. For aziridinations of N-Boc- or N-TcBoc-imines derived from aromatic aldehydes, see: (c) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M. ; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. See also: (d) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. In this paper, a Mannich-type adduct was observed as a by-product in 37% ee in catalytic asymmetric aza-Diels-Alder reaction of N-ethoxylcarbonyl α-imino ester with Danishefsky's diene.
10. Only a few successful examples of catalytic enantioselective reactions of imines bearing readily removable N-carbamates have been reported so far. For Friedel-Crafts-type reactions of N-carbamate-protected α-imino esters, see: (a) Sabby, S.; Bayon, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352. For Mannich-type reactions of N-Boc-imines derived from aromatic aldehydes, see: (b) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. For aziridinations of N-Boc- or N-TcBoc-imines derived from aromatic aldehydes, see: (c) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M. ; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. See also: (d) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. In this paper, a Mannich-type adduct was observed as a by-product in 37% ee in catalytic asymmetric aza-Diels-Alder reaction of N-ethoxylcarbonyl α-imino ester with Danishefsky's diene.
11. Only a few successful examples of catalytic enantioselective reactions of imines bearing readily removable N-carbamates have been reported so far. For Friedel-Crafts-type reactions of N-carbamate-protected α-imino esters, see: (a) Sabby, S.; Bayon, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352. For Mannich-type reactions of N-Boc-imines derived from aromatic aldehydes, see: (b) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. For aziridinations of N-Boc- or N-TcBoc-imines derived from aromatic aldehydes, see: (c) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M. ; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. See also: (d) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. In this paper, a Mannich-type adduct was observed as a by-product in 37% ee in catalytic asymmetric aza-Diels-Alder reaction of N-ethoxylcarbonyl α-imino ester with Danishefsky's diene.
12. Only a few successful examples of catalytic enantioselective reactions of imines bearing readily removable N-carbamates have been reported so far. For Friedel-Crafts-type reactions of N-carbamate-protected α-imino esters, see: (a) Sabby, S.; Bayon, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352. For Mannich-type reactions of N-Boc-imines derived from aromatic aldehydes, see: (b) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. For aziridinations of N-Boc- or N-TcBoc-imines derived from aromatic aldehydes, see: (c) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M. ; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. See also: (d) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435. In this paper, a Mannich-type adduct was observed as a by-product in 37% ee in catalytic asymmetric aza-Diels-Alder reaction of N-ethoxylcarbonyl α-imino ester with Danishefsky's diene.
13. Lectka et al. have reported chiral Cu(I)-catalyzed Mannich-type reactions using several N-sulfonyl-protected imines and deprotection of the Mannich-type adducts; see: Ferraris, D.; Dudding, T.; Young, B.; Drurry, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
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