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. Author manuscript; available in PMC: 2018 Jun 19.
Published in final edited form as: Angew Chem Int Ed Engl. 2017 May 22;56(26):7479–7483. doi: 10.1002/anie.201704069

Table 2.

Scope of the asymmetric [3+1]-cycloaddition reaction of enoldiazoacetate 1 with sulfur ylides 2.[a]

graphic file with name nihms912380u2.jpg
graphic file with name nihms912380t1.jpg
Yield(%)[b] ee(%)[c]
3a[e,f]: 72 83 (R2 = Me, Ar = Ph, R4 = Ph)
3b: 81 72 (R2 = Me, Ar = 4-ClC6H4, R4 = Ph)
3c: 82 70 (R2 = Me, Ar = 4-BrC6H4, R4 = Ph)
3d: 73 73 (R2= tBu, Ar = Ph, R4 = Ph)
graphic file with name nihms912380t2.jpg
Yield(%)[b] ee(%)[c] d.r.[d]
3e: 74 93 >20:1 (Ar = Ph, R4 = Me)
3f: 80 93 16:1 (Ar = 4-MeC6H4, R4 = Me)
3g: 82 98 14:1 (Ar = 4-MeOC6H4, R4 = Me)
3h: 72 99 >20:1 (Ar = naphthyl, R4 = Me)
3i: 80 95 18:1 (Ar = 4-ClC6H4, R4 = Me)
3j: 74 97 >20:1 (Ar = 4-BrC6H4, R4 = Me)
3k: 86 96 15:1 (Ar = 2-thiophenyl, R4 = Me)
3l: 58 97 16:1 (Ar = 4-CNC6H4, R4 = Ph)
[a]

Reaction conditions: 1 (0.24 mmol, 1.2 equiv) in dry DCM (1.0 mL) was added to a 1.0 mL DCM solution of 2 (0.20 mmol, 1.0 equiv), CuOTf·Tol1/2 (0.01 mmol), and L6 (0.012 mmol) under N2 within 1 h.

[b]

Yield of isolated product 3 based on the limiting reagent 2.

[c]

Enantiomeric excesses determined by HPLC analysis with a chiral stationary phase.

[d]

Diastereomeric ratios were determined by 1H NMR analysis of the reaction mixtures.

[e]

Reactions performed at −20°C.

[f]

Reactions performed for 48 hours.