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. 2020 Feb 3;5(5):2378–2396. doi: 10.1021/acsomega.9b03808

Table 3. Combined Yields and Product Ratios for the Synthesized Methoxymethylene Piperidines.

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entry R starting material Wittig products (%)a,b,c
1 2S-Me 2S-2a 2S-9 + 9′a (90)–Z:E, 1.2:1.0
2 2R-Me 2R-2′a 2R-9 + 9′b (75)–Z:E, 1.2:1.0
3 2R-Ph 2R-2c 2R-9 + 9′c (97)–Z:E, 1.0:1.0
4 2S-Ph 2S-2′c 2S-9 + 9′d (78)–Z:E, 1.1:1.0
a

Reaction conditions: [(Ph3)PCH2OCH3]Cl, LDA, 4 Ȧ MS, THF, −78 °C → rt, 16 h.

b

Isolated combined yield.

c

The ratio was determined by analysis of the 1H NMR spectra (entries 1–3) or derived from the isolated product yields (entry 4).