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Tetrahedron Letters

Volumn 28, Issue 49, 1987, Pages 6141-6144

Contrasteric carboximide hydrolysis with lithium hydroperoxide

(3) Evans, David A a Britton, Thomas C a Ellman, Jon A a

a HARVARD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001597804 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)61830-0 Document Type: Article

Times cited : (541)

References (19)

1
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2
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- Evans¹ Ennis² Le³ Mandel⁴ Mandel⁵

3
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- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6395-6397
- Evans¹ Britton² Dorow³ Dellaria⁴

4
- 84919146488
- Evans, D.A.; Britton, T.C. J. Am. Chem. Soc. in press.

5
- 0000687379
- (1987) Tetrahedron Lett. , vol.28 , pp. 1123-1126
- Evans¹ Ellman² Dorow³

6
- 0001594845
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 4346-4348
- Evans¹ Morrissey² Dorow³

7
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- Evans¹ Bartroli² Shih³

8
- 0000339580
- (1986) Tetrahedron Lett. , vol.27 , pp. 4957-4960
- Evans¹ Sjogren² Bartroli³ Dow⁴

9
- 0022490196
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6757-6761
- Evans¹ Weber²

10
- 0002049209
- (1987) Tetrahedron Lett. , vol.28 , pp. 39-42
- Evans¹ Sjogren² Weber³ Conn⁴

11
- 0000909681
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 4261-4263
- Evans¹ Chapman² Bisaha³

12
- 0022619194
- Also see refs. 7b. and 7d
- (1986) Tetrahedron Lett. , vol.27 , pp. 799-802
- Evans¹ Bender²

13
- 84919146487
- Aldol adducts generally give significantly higher yields with the Weinreb transamination method (ref. 9.).

14
- 0000409403
- While normal esters (i.e. EtOAc) are unreactive toward HOO-, active esters (e.g. PhOAc) react with a 400-fold rate enhancement relative to that of HO-, Also see ref. 14
- (1955) J. Am. Chem. Soc. , vol.77 , pp. 2519-2522
- Wiberg¹

15
- 84953502363
- An Alternative Procedure for the Aluminum-Mediated Conversion of Esters to Amides
- We thank Dr. Todd Jones for these results
- (1982) Synthetic Communications , vol.12 , pp. 989-993
- Levin¹ Turos² Weinreb³

16
- 84919146486
- To minimize possible side reactions resulting from hydroxy radical formation due to trace transition metals, we have routinely employed BHT-stabilized THF and redistilled water.

17
- 33947322034
- For a discussion of this point as it pertains to ester hydrolysis see
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 2622-2637
- Jencks¹ Gilchrist²

18
- 0000155765
- -, the so called alpha-effect. See, and references contained therein, For a critical review on the origin of the alpha effect see
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 2349-2353
- Evanseck¹ Blake² Jorgensen³

19
- 84985083786
- The α-Effect: A Critical Examination of the Phenomenon and Its Origin
- (1985) Israel Journal of Chemistry , vol.26 , pp. 313-319
- Hoz¹ Buncel²

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