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Tetrahedron Letters

Volumn 34, Issue 35, 1993, Pages 5563-5566

Studies directed toward the design of chiral acylating agents. The utility of chiral N-benzoylimides in enantioselective alcohol acylation

(3) Evans, David A a Anderson, James C a Taylor, Marta K a

a HARVARD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0027160610 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)73882-2 Document Type: Article

Times cited : (75)

References (26)

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2
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- Chen¹ Sih²

3
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4
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5
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- This is a related strategy to that employed by Horeau see, and references cited therein
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- Weidman¹ Horeau²

6
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- Diacylimides and their sulfur counterparts are well known as effective acylating agents. For several recent studies see:
- (1990) Tetrahedron Lett. , vol.31 , pp. 243-246
- Kikugawa¹ Mitsui² Sakamoto³ Kawase⁴ Tamiya⁵

7
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- Yamada¹

8
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- Yamada¹

9
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- (1987) Tetrahedron Lett. , vol.28 , pp. 6141-6144
- Evans¹ Britton² Ellman³

10
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- See the transformation of 9 → 14 (Scheme III) in this study.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1063-1072
- Evans¹ Ellman²

11
- 0001854037
- (4S)-tert-butyl-2-oxazolidinone (3) was prepared from (S)-tert-leucinol (Ref 12) according to the general procedure reported by us, in a yield of 88%: mp 105.8–106.4 °C. The N-benzoylation of 3 to afford 1b was carried out in analogy to a related acylation
- (1989) Organic Syntheses , vol.68 , pp. 77-82
- Gage¹ Evans²

12
- 0002062227
- 3: C, 68.00; H, 6.93; N, 5.66. Found: C, 67.95; H, 7.02; N, 5.56.
- (1989) Organic Syntheses , vol.68 , pp. 83-91
- Gage¹ Evans²

13
- 0344887064
- This reactivity trend is consistent with the pKa comparison between the 2-oxazolidinone moiety (pKa 20.5/DMSO) and phenol (pKa 18/DMSO) which provides a qualitative measure of leaving group potential of the indicated acyl substituent. These measurements have been carried out by F. G. Bordwell. For a general tabulation of acidity data in DMSO see:
- (1988) Accounts Chem. Res. , vol.21 , pp. 456-463
- Bordwell¹

14
- 33845278614
- The fact that 4-benzyl-2-oxazolidone is ca. 4 pKa units more acidic than related noncyclic amides and urethanes may be attributed to the same effects which have been identified in enhancing the CH acidity of lactones over related ester substrates. For a discussion of this issue see:
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1872-1874
- Wiberg¹ Laidig²

15
- 33947322034
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 2622-2637
- Jencks¹ Gilchrist²

16
- 84918737391
- With 2 equiv of racemic alcohol the reaction of 1b under identical conditions proceeds to ∼80% conversion after 24 h; however, formation of the bromomagnesium alkoxide with MeMgBr (vide infra), in the presence of 1 equiv of tetramethylethylenediamine affords complete reaction with 1b in 1 h at 0°C providing the (R) benzoate in 49% ee.

17
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- (1985) J. Org. Chem. , vol.50 , pp. 2622-2624
- Rathke¹ Cowan²

18
- 84918758843
- 3).

19
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- (1993) J. Org. Chem. , vol.58 , pp. 3568-3571
- McKennon¹ Meyers² Drauz³ Schwarm⁴

20
- 84918750431
- 2/N-methylpiperidine to form the magnesium alkoxides afforded slightly higher acyl transfer enantioselectivities.

21
- 84918742628
- Except for the N-β-naphthoyl imide which afforded comparable selectivities to the benzoyl residues in these acyl transfer reactions.

22
- 0026014628
- Absolute configurational assignments of the benzoates described in entries A-F were made via their derived 2° alcohols. See, and references cited therein
- (1991) Tetrahedron , vol.47 , pp. 7645-7662
- Janssen¹ Klunder² Zwannenburg³

23
- 2142858450
- These assignments were confirmed by the recently published NMR method for the assignment of absolute configuration of secondary alcohols:
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092-4096
- Ohtani¹ Kusumi² Kashman³ Kakisawa⁴

24
- 84918733475
- The authors wish to thank M. J. Scott and A. R. Muci for carrying out the X-ray analysis.

25
- 84918738858
- The dihedral angle between the aryl and CO substituents is 37.7°.

26
- 84918728644
- We have obtained numerous X-ray structures of 4-benzyl- and isopropyl-substituted N-acyloxazolidinones. This is the first instance where a deviation from planarity of the imide nitrogen has been observed.

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