Diastereofacial selection in ring-closure reactions and folding-strain stereocontrol

Chemistry - A European Journal

Volumn 4, Issue 12, 1998, Pages 2397-2404

  Tokoroyama, Takashi ^a  

^a 3 25 1 Makizuka dai ^*  (Japan)

Author keywords

Conformation analysis; Folding strain stereocontrol; Ring closure; Stereoselective synthesis; Transition states

Indexed keywords

CONFORMATIONAL TRANSITION; CYCLIZATION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031741997     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981204)4:12<2397::AID-CHEM2397>3.0.CO;2-D     Document Type: Review

References (75)

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65. In addition, we investigated the diastereoface-selective cyclization of 5,6-dimethyl-8-trimethylsilyl-6-octanals, which led to successful syntheses of marine natural products: a) K. Asao, H. Iio, T. Tokoroyama, Tetrahedron Lett. 1989, 30, 6397-6400; b) K. Asao, H. Iio, T. Tokoroyama, Tetrahedron Lett. 1989, 30, 6401-6404; c) K. Asao, H. Iio, T. Tokoroyama, Chem. Lett. 1989, 6401-6404.
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72. On the effect of controlling substituents to the diastereofacial selectivity of the IDA reactions, see for examples: a) W. R. Roush, M. Kageyama, R. Riva, B. B. Brown, J. S. Warmus, J. Org. Chem. 1991, 56, 1192-1210; b) J. A. Marshall, J. Grote, J. E. Audia, J. Org. Chem. 1987 52, 1236-1245; c) H. C. Kolb, S. V. Ley, R. N. Sheppard, A. M. Z. Slawin, S. C. Smith, D. J. Williams, A. Wood, J. Chem. Soc. Perkin Trans. 1, 1992, 2763-2777 and references cited therein.
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