SCOPUS 정보 검색 플랫폼

Volumn 24, Issue 27, 1983, Pages 2733-2736

Development of chiral β-dicarbonyl equivalents. Enantiodivergent alkylation of aspartic acid.

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001034524 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)88008-9 Document Type: Article

Times cited : (39)

References (15)

2
- 0013551093
- Stereoselective methylation of β-hydroxylactone dianions
- For representative examples:
- (1982) Tetrahedron Letters , pp. 3055
- Chamberlain¹ Dezube²

5
- 84985053359
- Herstellung vonerythro-2-Hydroxybernsteins�ure-Derivaten aus �pfels�ureester. Vorl�ufige Mitteilung
- (1980) Helvetica Chimica Acta , vol.63 , pp. 197
- Seebach¹ Wasmuth²

6
- 84943966860
- �ber die Stereospezifit�t der ?-Alkylierung von ?-Hydroxycarbons�ureestern. Vorl�ufige Mitteilung
- (1979) Helvetica Chimica Acta , vol.62 , pp. 2825
- Fráter¹

7
- 84985560897
- Alkylation of Amino Acids without Loss of Optical Activity:α- andβ-Alkylation of an Aspartic Acid Derivative
- For related studies:
- (1981) Angewandte Chemie International Edition in English , vol.20 , pp. 971
- Seebach¹ Wasmuth²

10
- 0347258491
- Highly Regioselective Reduction of Unsymmetrical Cyclic Anhydrides to Lactones with Hindered Trialkylborohydrides
- and references cited therein
- (1982) HETEROCYCLES , vol.18 , pp. 265
- Krishnamurthy¹ Vreeland²

12
- 84918409753
- The lactone dianions were formed by treating 3a or 3b with about 2.1 eg of base in THF at −78°C for 15 min. Subsequent alkylation took place within 2h at −78°C. We observed highest stereoselectivity when the enolate was rapidly introduced (cannula) to a chilled solution of the electrophile in THF.

13
- 84918409752
- However, alkkylation was very slow and incomplete when only 1 eq of base was employed. Deprotonating with 2.1 eq of base (15 min at −78°C) resulted in a species that condensed at a reasonable rate 91 to 4 h at −78°C, . No deleterious effect upon stereoselectivity has been observed by the presence of excess base.

14
- 84918424463
- Compare with, as as references 2c-e.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1137
- Evans¹ Ennis² Mathre³ Still⁴ Kahn⁵ Mitra⁶

15
- 0002714675
- Rapid chromatographic technique for preparative separations with moderate resolution
- For example, inthe case R=Me, the mixture of 6a/6b is resolved by simple flash chromatography:
- (1978) The Journal of Organic Chemistry , vol.43 , pp. 2923

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