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. Author manuscript; available in PMC: 2011 Mar 25.
Published in final edited form as: Org Lett. 2008 Mar 13;10(7):1485–1488. doi: 10.1021/ol8002942

Table 3.

Scope of the [(Rp,S)-COP-Cl]2-Catalyzed Rearrangement of (E)-O-Allyl Carbamothioates

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entry R1 R2 time, hc product
compd yield %d ee %e
1b n-Pr 1-azetinyl 15 ent-11c 98 83
2b n-Pr Me2 18 ent-11a 72 82
3 CH2CH(CH3)2 1-azetinyl 42 14a 85 80
4 CH2OTBDMS 1-azetinyl 20 14b 85 88
5 CH2OTBDMS Me2 18 15a 97 87f,g
6 CH2OTIPS 1-azetinyl 42 14c 99 87f
7 CH2OTBDPS 1-azetinyl 42 14d 86 76f
8 CH2OH 1-azetinyl 13 14e 55 61
9 CH2NPh(Boc) 1-azetinyl 44 14f 68 71
10 CH2NPh(Boc) Me2 43 15b 77 81
11 (CH2)2COMe 1-azetinyl 11 14g 85 76
a

Substrate concentration = 0.5 M.

b

Sp,R enantiomer of [COP–Cl]2 was used.

c

Time for disappearance of starting material by TLC analysis.

d

Yield of product after purification by column chromatography.

e

Determined by SFC analysis using a chiral stationary phase; results from duplicate experiments agreed within ± 1%.

f

Determined after conversion of the product to alcohol 14e.

g

Determined by GC analysis using a chiral stationary phase; results from duplicate experiments agreed within ±2%.