Intermolecular N-alkylation of amines under conditions of the Mitsunobu reaction: A new solid-phase synthesis of tertiary benzylamines

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1841-1844

  Zaragoza, Florencio ^a   Stephensen, Henrik ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

Amino acids and derivatives; Benzylation; Mitsunobu reactions; Solid phase synthesis

Indexed keywords

ALCOHOL; AMINE; AMMONIUM DERIVATIVE; BENZYLAMINE; IODIDE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034635902     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00028-9     Document Type: Article

References (16)

1. Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127-164; Hughes, D. L. Org. React. 1992, 42, 335-656; Itô, S.; Tsunoda, T. Pure Appl. Chem. 1999, 71, 1053-1057.
2. Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127-164; Hughes, D. L. Org. React. 1992, 42, 335-656; Itô, S.; Tsunoda, T. Pure Appl. Chem. 1999, 71, 1053-1057.
3. Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127-164; Hughes, D. L. Org. React. 1992, 42, 335-656; Itô, S.; Tsunoda, T. Pure Appl. Chem. 1999, 71, 1053-1057.
4. Edwards, M. L.; Stemerick, D. M.; McCarthy, J. R. Tetrahedron 1994, 50, 5579-5590.
5. Jia, Z. J. Synlett 1999, 565-566; Walker, M. A. J. Org. Chem. 1995, 60, 5352-5355.
6. Jia, Z. J. Synlett 1999, 565-566; Walker, M. A. J. Org. Chem. 1995, 60, 5352-5355.
7. Nikam, S. S.; Kornberg, B. E.; Rafferty, M. F. J. Org. Chem. 1997, 62, 3754-3757. Examples of intermolecular N-alkylations of amines with other phosphorus-derived reagents have been reported: Kubota, T.; Miyashita, S.; Kitazume, T.; Ishikawa, N. J. Org. Chem. 1980, 45, 5052-5057; Tanigawa, Y.; Murahashi, S.; Moritani, I. Tetrahedron Lett. 1975, 471-472; Castro, B.; Selve, C. Bull. Soc. Chim. Fr. 1971, 4368-4373.
8. Nikam, S. S.; Kornberg, B. E.; Rafferty, M. F. J. Org. Chem. 1997, 62, 3754-3757. Examples of intermolecular N-alkylations of amines with other phosphorus-derived reagents have been reported: Kubota, T.; Miyashita, S.; Kitazume, T.; Ishikawa, N. J. Org. Chem. 1980, 45, 5052-5057; Tanigawa, Y.; Murahashi, S.; Moritani, I. Tetrahedron Lett. 1975, 471-472; Castro, B.; Selve, C. Bull. Soc. Chim. Fr. 1971, 4368-4373.
9. Nikam, S. S.; Kornberg, B. E.; Rafferty, M. F. J. Org. Chem. 1997, 62, 3754-3757. Examples of intermolecular N-alkylations of amines with other phosphorus-derived reagents have been reported: Kubota, T.; Miyashita, S.; Kitazume, T.; Ishikawa, N. J. Org. Chem. 1980, 45, 5052-5057; Tanigawa, Y.; Murahashi, S.; Moritani, I. Tetrahedron Lett. 1975, 471-472; Castro, B.; Selve, C. Bull. Soc. Chim. Fr. 1971, 4368-4373.
10. Nikam, S. S.; Kornberg, B. E.; Rafferty, M. F. J. Org. Chem. 1997, 62, 3754-3757. Examples of intermolecular N-alkylations of amines with other phosphorus-derived reagents have been reported: Kubota, T.; Miyashita, S.; Kitazume, T.; Ishikawa, N. J. Org. Chem. 1980, 45, 5052-5057; Tanigawa, Y.; Murahashi, S.; Moritani, I. Tetrahedron Lett. 1975, 471-472; Castro, B.; Selve, C. Bull. Soc. Chim. Fr. 1971, 4368-4373.
11. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Itô, S. Tetrahedron Lett. 1996, 37, 2463-2466; Walker, M. A. Tetrahedron Lett. 1996, 37, 8133-8136; Bernotas, R. C.; Cube, R. V. Tetrahedron Lett. 1991, 32, 161-164.
12. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Itô, S. Tetrahedron Lett. 1996, 37, 2463-2466; Walker, M. A. Tetrahedron Lett. 1996, 37, 8133-8136; Bernotas, R. C.; Cube, R. V. Tetrahedron Lett. 1991, 32, 161-164.
13. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Itô, S. Tetrahedron Lett. 1996, 37, 2463-2466; Walker, M. A. Tetrahedron Lett. 1996, 37, 8133-8136; Bernotas, R. C.; Cube, R. V. Tetrahedron Lett. 1991, 32, 161-164.
14. Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967-2971.
15. 2 (369.34): C, 58.54; H, 4.91; N, 3.79. Found: C, 58.54; H, 4.91; N, 3.89.
16. Both enantiomers of proline were N-alkylated with 2-naphthylmethanol and analyzed by HPLC on a chiral stationary phase.