Asymmetric synthesis of enantio-enriched acyclic α-amino alkylstannanes and rearrangement behavior of carbanions thereof

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1239-1242

  Tomoyasu, Takahiro ^a,b   Tomooka, Katsuhiko ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; CARBON; LITHIUM; LITHIUM DERIVATIVE; TIN;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037415462     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02811-3     Document Type: Article

References (33)

1. Reviews: (a) Marshall, J. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, pp. 975-1014; (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209; (c) Nakai, T.; Tomooka, K. Pure Appl. Chem. 1997, 69, 595-600.
2. Reviews: (a) Marshall, J. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, pp. 975-1014; (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209; (c) Nakai, T.; Tomooka, K. Pure Appl. Chem. 1997, 69, 595-600.
3. Reviews: (a) Marshall, J. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, pp. 975-1014; (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209; (c) Nakai, T.; Tomooka, K. Pure Appl. Chem. 1997, 69, 595-600.
4. Review: Vogel C. Synthesis. 1997;497-505.
5. A tin-lithium transmetalative method provides easy access to configurationally stable α-amino alkyllithiums: (a) Chong, J. M.; Park. S. B. J. Org. Chem. 1992, 57, 2220-2222; (b) Burchat, A. F.; Chong, J. M.; Park. S. B. Tetrahedron Lett. 1993, 34, 51-54; (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763-5769.
6. A tin-lithium transmetalative method provides easy access to configurationally stable α-amino alkyllithiums: (a) Chong, J. M.; Park. S. B. J. Org. Chem. 1992, 57, 2220-2222; (b) Burchat, A. F.; Chong, J. M.; Park. S. B. Tetrahedron Lett. 1993, 34, 51-54; (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763-5769.
7. A tin-lithium transmetalative method provides easy access to configurationally stable α-amino alkyllithiums: (a) Chong, J. M.; Park. S. B. J. Org. Chem. 1992, 57, 2220-2222; (b) Burchat, A. F.; Chong, J. M.; Park. S. B. Tetrahedron Lett. 1993, 34, 51-54; (c) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763-5769.
8. Gawley R.E., Zhang Q., Campagna S. J. Am. Chem. Soc. 117:1995;11817-11818.
9. Peterson D.J., Ward J.F. J. Organomet. Chem. 66:1974;209-217.
10. Coldham I. J. Chem. Soc., Perkin Trans. 1. 1993;1275-1276.
11. The first synthesis of N-allyl-N-Boc-α-amino alkylstannane was reported by Chong's group. However, they have not commented on the aza-Wittig rearrangement thereof, see: Ref. 3a.
12. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
13. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
14. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
15. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
16. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
17. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
18. A wide variety of methods have been reported for the preparation of acyclic α-amino alkylstannanes but all give primary or racemic products. (a) Peterson, D. J. J. Am. Chem. Soc. 1971, 93, 4027-4031; (b) Quintard, J.-P.; Elissondo, B.; Jousseaume, B. Synthesis 1984, 495-498; (c) Elissondo, B.; Verlhac, J.-B.; Quintard, J.-P.; Pereyre, M. J. Organomet. Chem. 1988, 339, 267-275; (d) Ahlbrecht, H.; Baumann, V. Synthesis 1994, 770-772; (e) Pearson, W. H.; Stevens, R. P. Synthesis 1994, 904-906; (f) Katritzky, A. R.; Chang, H.-X.; Wu, J. Synthesis 1994, 907-908; (g) Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627-7630.
19. Marshall J.A., Gung W.Y. Tetrahedron Lett. 29:1988;1657-1660.
20. Chan C.M., Chong J.M. J. Org. Chem. 53:1988;5584-5586.
21. Tomooka K., Igarashi T., Nakai T. Tetrahedron Lett. 35:1994;1913-1916.
22. Chong's group has reported that enantio-enriched α-phthalimido alkylstannane can be prepared by the Mitsunobu reaction of enantio-enriched α-hydroxy alkylstannane and phthalimide, see: Ref. 3a.
23. N2 reaction with alkoxides has been reported: Tomooka K., Igarashi T., Nakai T. Tetrahedron Lett. 34:1993;8139-8142.
24. The enantiopurity of (R)-2,3 was determined by chiral HPLC analysis (Chiralcel OD-H, 0.46×25 cm).
25. 3) δ 15.5, 17.7, 32.6, 32.8, 40.3, 49.6, 60.5, 114.8, 125.6, 126.9, 128.3, 128.3, 130.0, 141.9, 142.8.
26. 1H NMR analysis after conversion (hydrazine hydrate/MTPACl) to a MTPA amide of (R)-6.
27. Treatment of (R)-2 with n-BuLi at -78→0°C led to complex mixtures of products.
28. Unfortunately, a previously developed synthetic method from (S)-1 was not applicable to the preparation of diallyl derivatives.
29. The intramolecular coordination between the lithium and the olefinic π-bond may play a very important role for configurational stability of α-amino alkyllithiums, see: Komine N., Tomooka K., Nakai T. Heterocycles. 52:2000;1071-1074.
30. In contrast, a similar reaction of N-allyl-N-Me-α-amino alkylstannane 13 gave no rearrangement product. Thus, the reasonable coordination ability of the olefinic π-bond in the transition state C appears to be well suited for aza-Wittig rearrangement.
31. Authentic samples of (S)-8 and (S,S)-9 were prepared as depicted below. The starting stannane (S)-14 (>95% ee) was prepared by our reported method, see: Tomooka K., Shimizu H., Inoue T., Shibata H., Nakai T. Chem. Lett. 1:1999;759-760.
32. Retention of stereochemistry in tin-lithium exchange reactions is well-known for the preparation of stereochemically defined α-hetero alkyllithiums, see: Pearson W.H., Lindbeck A.C., Kampf J.W. J. Am. Chem. Soc. 115:1993;2622-2636. and references cited therein.
33. Rearrangement products 11 and 12 were obtained as a complex mixture of several diastereomers. Thus, the enantiopurity of the products has not yet been determined.