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Organic Letters

Volumn 9, Issue 1, 2007, Pages 149-152

Highly selective acetate aldol additions using mesityl-substituted chiral auxiliaries

(2) Crimmins, Michael T a Shamszad, Mariam a

a UNIVERSITY OF NORTH CAROLINA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 THIAZOLINETHIONE; 3-HYDROXYBUTANAL; ACETIC ACID DERIVATIVE; ALDEHYDE; ALDOL; OXAZOLIDINONE DERIVATIVE; THIAZOLIDINE DERIVATIVE; THIAZOLINE-2-THIONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOISOMERISM;

ACETATES; ALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; OXAZOLIDINONES; STEREOISOMERISM; THIAZOLIDINES;

EID: 33846463792 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol062688b Document Type: Article

Times cited : (87)

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28
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29
- 33846411919
- (S)-N-Acetyloxazolidinethione can be accessed from the same sequence of steps, starting from (S)-(-)-2-methyl-2-propanesulfmamide.
- (S)-N-Acetyloxazolidinethione can be accessed from the same sequence of steps, starting from (S)-(-)-2-methyl-2-propanesulfmamide.

30
- 33846413039
- Typical aldol procedure using N-acetyloxazolidinethione 4: To a dry 25 mL round-bottom flask, under argon, was added N- acetyloxazolidinethione (0.263 g, 1.00 mmol) and 5 mL of CH2Cl 2 (0.2 M, The flask was cooled to -40°C. Titanium tetrachloride (neat, 0.22 mL, 2.00 mmol) was added, and the reaction mixture was stirred for 5 min. Diisopropyl-ethylamine (0.35 mL, 2.00 mmol) was then added. The solution was stirred for 2 h at -40°C and was then cooled to -78°C, whereupon the freshly distilled aldehyde (neat, 1.2 mmol) was added. The mixture was stirred for 4 h at -78°C, then quenched with half saturated ammonium chloride and warmed to room temperature. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2x, The combined organic layers were dried over NaSO4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography 20% EtOA
- 4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (20% EtOAc/ Hex). Yields and diastereoselectivities are listed in Table 1.

31
- 33846428485
- 3). For the lit. value of (R)-4-methyl- pentane-1,3-diol, see: (a) ref 10c.
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32
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35
- 33846462543
- (R)-N-Acetylthiazolidinethione can be accessed from the same sequence of steps, starting from (S)-(-)-2-methyl-2-propane-sulfinamide.
- (R)-N-Acetylthiazolidinethione can be accessed from the same sequence of steps, starting from (S)-(-)-2-methyl-2-propane-sulfinamide.

36
- 33846451123
- Typical aldol procedure using N-acetylthiazolidinethione 9: To a dry 25 mL round-bottom flask, under argon, was added N- acetylthiazolidinethione (0.307 g, 1.10 mmol) and 5.2 mL of CH 2Cl2 (0.2 M, The solution was cooled to -78°C, and titanium tetrachloride (neat, 0.12 mL, 1.10 mmol) was added and stirred for 5 min. Diisopropylethylamine (0.19 mL. 1.10 mmol) was added. The solution was stirred for 30 min at -78°C, whereupon the freshly distilled aldehyde (neat, 1.0 mmol) was added dropwise. The mixture was stirred for l h at -78°C, then quenched with half saturated ammonium chloride and warmed to room temperature. The layers were separated and the aqueous layer was extracted with CH2Cl2 2x, The combined organic layers were dried over NaSO4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography, 10% EtOAc/Hex to 20% EtOAc/Hex, Yields and diaste
- 4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography ( 10% EtOAc/Hex to 20% EtOAc/Hex). Yields and diastereoselectivities are listed in Table 2.

37
- 33846454422
- 3). For the lit. value of (R)-4-methyl- pentane-1,3-diol, see: (a) ref 10c.
- 3). For the lit. value of (R)-4-methyl- pentane-1,3-diol, see: (a) ref 10c.

38
- 0000031605
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- (1992) J. Org. Chem , vol.57 , pp. 1412
- Harada, T.¹ Kurokawa, H.² Kagamihara, Y.³ Tanaka, S.⁴ Inoue, A.⁵

39
- 33746919049
- Double diastereoselective acetate aldol reactions using phenyldichloroboryl enolates of chiral N-acetylthiazolidinethione reagents have recently been examined by Sammakia: Zhang, Y.; Sammakia, T. J. Org. Chem. 2006, 71, 6262.
- Double diastereoselective acetate aldol reactions using phenyldichloroboryl enolates of chiral N-acetylthiazolidinethione reagents have recently been examined by Sammakia: Zhang, Y.; Sammakia, T. J. Org. Chem. 2006, 71, 6262.

40
- 33846447156
- Aldehyde 12a was prepared via an acetate aldol addition. Aldehyde 12b was prepared via a propionate aldol addition previously reported by our laboratory (ref 4a). See Supporting Information for detailed procedure.
- Aldehyde 12a was prepared via an acetate aldol addition. Aldehyde 12b was prepared via a propionate aldol addition previously reported by our laboratory (ref 4a). See Supporting Information for detailed procedure.

41
- 33846433226
- 2NEt, and 1.1 equiv of thiazolidinethione 9. See Supporting Information for detailed procedure.
- 2NEt, and 1.1 equiv of thiazolidinethione 9. See Supporting Information for detailed procedure.

42
- 33846444054
- 2NEt, and 1.5 equiv of thiazolidinethione 9. See Supporting Information for detailed procedure.
- 2NEt, and 1.5 equiv of thiazolidinethione 9. See Supporting Information for detailed procedure.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.