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Volumn 6, Issue 4, 1995, Pages 853-856

An asymmetric route to the 5,6-dihydro-4H-1,3-thiazine skeleton via an asymmetric hetero diels-alder reaction

Author keywords

[No Author keywords available]

Indexed keywords

1,3 THIAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0028950963 PISSN: 09574166 EISSN: 1362511X Source Type: Journal
DOI: 10.1016/0957-4166(95)00087-6 Document Type: Article

Times cited : (36)

References (14)

1
- 0000946892
- (1979) Bull. Soc. Chim. Fr. , vol.2 , pp. 347-349
- Meslin¹ Quiniou²

2
- 84947677001
- SUBSTITUTED 1-THIA-3-AZA -1,3-BUTADIENE: DIELS-ALDER REACTION WITH METHYLACRYLATE. DETERMINATION OF ACTIVATION PARAMETERS
- (1989) Phosphorus, Sulfur, and Silicon and the Related Elements , vol.42 , pp. 15-19
- Chehna¹ Pradère² Quiniou³ Le Botlan⁴ Toupet⁵

4
- 0028264476
- For a recent review on asymmetric hetero Diels-Alder reactions, see:
- (1994) Synthesis , pp. 535-551
- Waldmann¹

5
- 84985598285
- Concerning the Mechanism of the Asymmetric Diels-Alder Reaction: First Crystal Structure Analysis of a Lewis Acid Complex of a Chiral Dienophile
- See also:
- (1985) Angewandte Chemie International Edition in English , vol.24 , pp. 112-114
- Poll¹ Metter² Helmchen³

6
- 37049081428
- Diastereoselective imino ester cycloadditions. Enantioselective synthesis of azabicyclo[2.2.1]heptenes
- (1992) Journal of the Chemical Society, Chemical Communications , pp. 786-788
- Hamley¹ Helmchen² Holmes³ Marshall⁴ MacKinnon⁵ Smith⁶ Ziller⁷

7
- 33845280186
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1238-1256
- Evans¹ Chapman² Bisaha³

9
- 84914092072
- 3, δ): 2.41 (s, 6H), 2.82 (dd, J = 8.6 Hz, 13.7 Hz, 1H), 3.14 (dd, J = 3.7 Hz, 12.2 Hz, 1H), 3.30 (dd, J = 3.2 Hz, 13.7 Hz, 1H), 3.47 (dd, J = 12.2 Hz, 12.2 Hz, 1H), 4.24 (m, 2H), 4.49 (ddd, J = 3.7 Hz, 10.1 Hz, 12.2 Hz, 1H), 4.71 (d, J = 10.1 Hz, 1H), 4.79 (m, 1H), 7.32 (m, 8H), 7.85 (m, 2H).

10
- 84914092071
- Toupet, L. Université de Rennes. Details of the crystal structure of 5b will be reported in a forthcoming full paper.

11
- 84914092070
- Additional results to be reported in a forthcoming full paper strongly suggest that 5b is a kinetic adduct. Studies are in progress in order to best understand the origin of the exo selectivity.

13
- 84914092068
- We have experienced considerable difficulties in removing the 2-oxazolidinone chiral auxiliary from adduct 5b probably due to steric shielding of the exocylic carbonyl group. Transesterification with lithium benzyloxide gave no more than 40% yield of the corresponding 3. Other protocols employing lithium hydroxide, basic hydrogen peroxide or lithium borohydride proved to be ineffective in the case at hand.

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