Consecutive Intramolecular Azomethine Ylid Cycloaddition - Pummerer Rearrangement as a Strategy for the Synthesis of Enantiomerically Pure 5-(Hydroxymethyl)prolines

Synlett

Volumn 1996, Issue 10, 1996, Pages 1010-1012

  Harwood, L M ^a   Lilley, I A ^b  

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001941951     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5648     Document Type: Article

References (10)

1. Harwood, L. M.; Lilley, I. A. Tetrahedron Lett., 1993, 34, 537.
2. Harwood, L. M.; Kitchen, L. C. Tetrahedron Lett., 1993, 34, 6603.
3. Larcheveque, M.; Sanner, C.; Azerad, R.; Buisson, D. Tetrahedron, 1988, 44, 6407.
4. For reviews covering much of this work see: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press. Oxford, 1989; Williams, R. M. Aldrichimica Acta, 1992, 25, (1), 11. Later work has led to improvements in generating the carbanionic species of morpholinones: Baldwin, J. E.; Lee, V.; Schofield, C. J. Heterocycles 1992, 34, 903.
5. For reviews covering much of this work see: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press. Oxford, 1989; Williams, R. M. Aldrichimica Acta, 1992, 25, (1), 11. Later work has led to improvements in generating the carbanionic species of morpholinones: Baldwin, J. E.; Lee, V.; Schofield, C. J. Heterocycles 1992, 34, 903.
6. For reviews covering much of this work see: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press. Oxford, 1989; Williams, R. M. Aldrichimica Acta, 1992, 25, (1), 11. Later work has led to improvements in generating the carbanionic species of morpholinones: Baldwin, J. E.; Lee, V.; Schofield, C. J. Heterocycles 1992, 34, 903.
7. 2,5-Dihydroxymethylpyrrolidine derivatives have utility as chiral auxiliaries (Katsuki, T.; Yamaguchi, M. J. Syn. Org. Chem. Jpn., 1986, 44, 532) and show glucosidase inhibitory activity (for example see: Thompson, D. K.; Hubert, C. N.; Wightman, R. H. Tetrahedron, 1993, 49, 3827 and particularly the references to Fleet and co-workers contained within).
8. 2,5-Dihydroxymethylpyrrolidine derivatives have utility as chiral auxiliaries (Katsuki, T.; Yamaguchi, M. J. Syn. Org. Chem. Jpn., 1986, 44, 532) and show glucosidase inhibitory activity (for example see: Thompson, D. K.; Hubert, C. N.; Wightman, R. H. Tetrahedron, 1993, 49, 3827 and particularly the references to Fleet and co-workers contained within).
9. Leonard, N. J.; Johnson, C. R. J. Org. Chem., 1962, 27, 282.
10. 6) δ = 1.78 (dt, J = 12.6 Hz, 7.8 Hz, 1H), 2.10 (dd, J = 11.6 Hz, 1.4 Hz, 1H), 2.53 (ddd, J = 13.5 Hz, 8.9 Hz, 2.7 Hz, 1H), 2.75 (s, 3H), 2.78 (dd, J = 11.6 Hz, 6.6 Hz, 1H), 2.86-2.93 (m, 1H),