A facile access to chiral 4-isopropyl-, 4-benzyl-, and 4-phenyloxazolidine-2-thione

Journal of Organic Chemistry

Volumn 69, Issue 11, 2004, Pages 3990-3992

  Wu, Yikang ^a   Yang, Yong Qing ^a   Hu, Qi ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; HYDROGEN PEROXIDE; POTASH;

AUXILIARIES; STARTING MATERIALS;

KETONES;

2 OXAZOLIDINETHIONE; 4 BENZYLOXAZOLIDINE 2 THIONE; 4 ISOPROPYLOXAZOLIDINE 2 THIONE; 4 PHENYLOXAZOLIDINE 2 THIONE; AMINOALCOHOL; HYDROGEN PEROXIDE; OXAZOLIDINE DERIVATIVE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; OXIDATION; RING CLOSING METATHESIS; STOICHIOMETRY; SYNTHESIS;

EID: 2442666548     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049799d     Document Type: Article

References (32)

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26. Compared with 1b and 1c, 1a (and some of its derivatives) is easier to crystallize. Besides, both the (S)- and (R)-isomer of phenylglycine (the precursor of 2a and its (R)-enantiomer, respectively) are commercially available at rather low prices.
27. 3 (0.5 molar equiv) in EtOH at 50 °C for 1 h did not lead to any discernible reactions at all.
28. 3 from 0.5 to 0.2 molar equiv still led to 1a in 69% yield instead of the "theoretical" 40% (entry 12).
29. 3/MeOH procedure (ref 7a) on the same scale.
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32. The elemental analysis and the melting point measuring were performed on the "crude" product without any purification.