(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide

Uses

Reactant for:

• Rhodium-catalyzed asymmetric hydrogenation reactions
• Wittig reaction
• Wittig methylenation
• Preparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via double aza-Michael addition reaction
• Stereoselective preparation of of α-fluoro-α,β-unsaturated esters via deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydes
• Wittig chain extension reactions

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Example 3: The general procedure for the synthesis of (tert-butoxycarbonylmethyl)triphenylphosphonium bromide from tert-butyl bromoacetate and triphenylphosphine is as follows: In another embodiment, the functionalized lactone comprises a carboxylate protecting group as shown in Fig. 1. 10. Ylide synthesis was carried out using the following reagents and conditions: (a) triphenylphosphine (PPh3), benzene (C6H6), reaction time 12 h at room temperature (rt); (b) 20% aqueous sodium hydroxide solution (NaOH, aq), reaction time 5 h at room temperature.

References

[1] Patent: US2007/265243, 2007, A1. Location in patent: Page/Page column 4
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 199 - 209
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 5, p. 1188 - 1208
[4] Patent: US2007/43088, 2007, A1. Location in patent: Page/Page column 5
[5] Organic Process Research and Development, 2009, vol. 13, # 4, p. 710 - 715