COMMUNICATIONS
Asymmetric Synthesis of Substituted Thiolanes
Enzyme Inc. or Sigma–Aldrich: Burkholderia (formerly
Pseudomonas) cepacia lipase (BCL, Lipase PS “AMANO”
IM), Candida rugosa lipase (Sigma L1754), lipase from
Pseudomonas fluorescens (Aldrich 534730), and Candida
antarctica lipase B (Sigma L4777). 1H and 13C NMR data
were recorded on a Bruker Avance 400 (100) MHz or
a Bruker Avance 500 (125) MHz spectrometer, respectively.
Chemical shifts are reported as d values (ppm) with CDCl3
(1H NMR d=7.26, 13C NMR d=77.0) as an internal stan-
dard. J values are given in Hertz (Hz). Analytical high per-
formance liquid chromatography (HPLC) with a chiral sta-
tionary phase was performed on HP-Agilent 1110 Series
controller, using a Daicel Chiralpak OJ column (4.6ꢁ
250 mm, 10 mm). Solvents for HPLC use were of spectro-
metric grade. Thin layer chromatography (TLC) was per-
formed on precoated Polygramꢂ SIL G/UV 254 silica plates
(0.20 mm, Macherey–Nagel), visualized with UV detection.
Flash column chromatography was performed on silica gel
60, 0.040–0.063 mm (SDS).
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General Procedure for Dynamic Systemic Resolution
The dynamic systems were generated by adding each nitro-
propene (1 equiv., 0.05 mmol), together with 2,5-dihydroxy-
1,4-dithiane 7 (0.5 equiv., 0.025 mmol) and tetramethylgua-
nidine (TMG, 0.025 mmol) in dry toluene (0.6 mL). After
adding acylating reagent (3 equiv., 0.15 mmol), the solution
was transferred to a 1.5-mL sealed-cap vial containing BCL
(immobilized on diatomaceous earth, Amano Enzyme Inc.,
transesterification activity >500 u/g, 150 mg), ZnI2
(0.5 equiv., 0.025 mmol) and ground 4 ꢃ molecular sieves
under an argon atmosphere, pre-dried for 2 days before use.
The reaction vials were subsequently kept at room tempera-
ture under continuous shaking (around 500 rpm).
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Acknowledgements
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This work was in part supported by the Swedish Research
Council and the Royal Institute of Technology. YZ thanks the
China Scholarship Council for a special scholarship award.
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