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Tetrahedron Letters

Volumn 28, Issue 45, 1987, Pages 5423-5426

Stereoselection in the reaction of acid halides and vinylogous urethanes

(3) Schlessinger, Richard H a Tata, James R a Springer, James P b

a UNIVERSITY OF ROCHESTER (United States)

b Merck Sharp and Dohme Research Laboratories Rahway New Jersey 07065 USA ^*

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001044306 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)96744-3 Document Type: Article

Times cited : (5)

References (19)

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2
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- were the first group to examine condensation-reduction reaction of simple acid halides with amide enolates.
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- Evans¹ Ennis² Le³

3
- 0000624803
- Other groups that have examined similar transformations include
- (1984) Tetrahedron Lett. , vol.25 , pp. 6015
- Ito¹ Katsuki² Yamaguchi³

4
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5
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6
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- describe the condensation of an enolate possessing a chiral auxiliary with a chiral anhydride.
- (1983) Tetrahedron Lett , vol.24 , pp. 4805
- DiPardo¹ Bock²

7
- 0001399730
- For an excellent review of the diastereoselective behavior of aldehydes with nucleophiles, see, F.L. Boschke, Springer-Verlag, New York
- (1980) Topics in Current Chemistry , vol.88 , pp. 145-162
- Anh¹

8
- 58149505663
- Neutron diffraction study of liquid acetyl chloride.
- For experimental work (neutron diffraction) on the structure of acetyl chloride in the liquid phase, see, and references cited therein.
- (1980) Bulletin of the Chemical Society of Japan , vol.53 , pp. 1510
- Ohtomo¹ Arakawa²

9
- 8244229069
- (1986) J. Org. Chem. , vol.51 , pp. 3068
- Adams¹ Schlessinger² Tata³ Venit⁴

10
- 33748671692
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 357
- Schlessinger¹ Poss²

11
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- We thank Professor Danishefsky (Yale University) for the sample of 10.
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- Danishefsky¹ Kato² Askin³ Kerwin⁴

12
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- Dale¹ Dull² Mosher³

13
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- (1985) J. Org. Chem. , vol.50 , pp. 1979
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14
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- Complete 1H NMR data for these lactones are available in the supplemental material.
- (1975) Bull. Chem. Soc. Jpn. , vol.48 , pp. 1254
- Aburaki¹ Konishi² Kinoshita³

15
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- D −92° (ethanol, no concentration given) has been reported by
- (1963) Tetrahedron , vol.19 , pp. 1675
- Ott¹ Frey² Hofman³

16
- 84919126362
- The trimethylacetic acid-derived mixed anhydride as well as the 2-thiopyridine ester analogues of compounds 4 and 26 were also examined in this study. Neither the mixed anhydride nor the 2-thiopyridine ester systems reacted with the ketene acetal enamine 3. However, both systems reacted with the enolate 2 giving rise to the same diastereomeric ratio of products as their acid chloride analogues.

17
- 0019119204
- (1980) Agric. Biol. Chem. , vol.44 , pp. 199
- Tanaka¹ Yamashita²

18
- 84919126361
- Table Removed, For some of the acid halide condensation hydricle reduction examples reported herein, we have also carried out their aldol counterparts using the lithium enolate 2 at essentially the same concentrations and the same temperatures. These results are tabulated below.

19
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- (1977) Nouveau J. Chim. , vol.1 , pp. 61
- Anh¹ Eisenstein²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.