Synthesis of N-(tert-butoxycarbonyl)-N,O-isopropylidene serinal from serine methyl ester by a reduction-oxidation sequence

Synthesis

Volumn , Issue 5, 1997, Pages 527-529

  Dondoni, Alessandro ^a   Perrone, Daniela ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SERINE;

ARTICLE; CHROMATOGRAPHY; DRUG STABILITY; DRUG SYNTHESIS; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SEQUENCE HOMOLOGY; STEREOCHEMISTRY;

EID: 0030994242     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. (a) Dondoni, A.; Perrone, D. Synthesis 1993, 1162.
2. (b) Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939.
3. (c) Dondoni, A.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. J. Chem. Soc., Chem. Commun. 1994, 1731.
4. (d) Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4749.
5. (e) Dondoni, A.; Perrone, D.; Merino, P. J. Org. Chem. 1995, 60, 8074.
6. The syntheses of the ester 1 and aldehyde 2 were first reported by Garner: Garner, P. Tetrahedron Lett. 1984, 25, 5855. Compound 2, which has been considered as a penaldic acid equivalent, is often referred to as the Garner aldehyde.
7. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
8. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
9. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
10. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
11. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
12. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
13. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
14. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
15. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
16. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
17. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
18. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
19. For recent applications, see: (a) Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344. (c) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697. (d) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727. (e) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. (f) Soai, K.; Takahashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1257. (g) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C-G. Tetrahedron Lett. 1994, 35, 7775. (h) Moore, W. J.; Luzzio, F. A. Tetrahedron Lett. 1995, 36, 6599. (i) Ruan, F.; Yamamura, S.; Hakomori, S.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 6615. (j) Koskinen, A. M. P.; Hassila, H.; Myllymäki, V. T.; Rissanen, K. Tetrahedron Lett. 1995, 36, 5619. (k) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877. (l) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275. (m) Kozikowski, A. P.; Ding, Q.; Spiegel, S. Tetrahedron Lett. 1996, 37, 3279.
20. An additional point regarding the importance of the nitrogen protection of chiral α-amino carbonyl compounds stems from the control of the syn/anti selectivity (stereochemical tuning) of addition reactions by using singly and doubly protected nitrogen derivatives, see: Ref. 1.
21. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361. Garner, P.; Park, J. M. Org. Synth. 1991, 70, 18.
22. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361. Garner, P.; Park, J. M. Org. Synth. 1991, 70, 18.
23. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31.
24. Roush, W. R.; Hunt, J. A. J. Org. Chem. 1995, 60, 798.
25. A similar direct route has been reported via reduction of the Weinreb N-methoxyamide corresponding to the ester S-1. The aldehyde S-2 was obtained in 78 % yield (38 % overall yield from N-Boc serine), see: Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H.-P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865.
26. The non-enolizable nature and stability of the alcohol 3 at r.t. make this compound suitable for a long time storage and easy handling. Therefore the alcohol 3 is a convenient ultimate precursor of the aldehyde 2.
27. Tidwell, T. T. Synthesis 1990, 857.
28. Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046.
29. This yield has been calculated after repetition of the whole preparation in different weight scales, from 0.1 to 10 g.
30. Perrin, D. D.; Armarego, W. L. Purification of Laboratory Chemicals; Pergamon: New York, 1988.
31. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.