Library and Reading Room

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Citation for the assigned Paper:

Boeckman, R. K.; Wang, H.; Rugg, K. W.; Genung, N. E.; Chen, K.; Ryder, T. R. Org. Lett. 2016, 18 (23), 6136–6139.

Papers Related to this mechanism:

Not cited in our paper:

1.Ranoux, A.; Lemiègre, L.; Benoit, M.; Guégan, J.-P.; Benvegnu, T. Eur. J. Org. Chem. 2010, 2010 (7), 1314–1323.

2.Yamazaki, T.; Mano, N.; Hikage, R.; Kaneko, T.; Kawasaki-Takasuka, T.; Yamada, S. Tetrahedron 2015, 71 (42), 8059–8066.

Citation 31 in our paper:

3.Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25 (21), 2183–2186.

This paper describes the HWE reaction using lithium as the metal cation and an amine. Lithium cations form a tight complex with the phosphonate-stabilized carbanion (Fig. 4, right). This allows the use of amines and base-sensitive phosphonates in the formation of olefins when using an HWE reaction. The study of this technique in HWE is useful because conventional methods for HWE reactions using NaH or potassium carbonate can lead to complications when the reagents are base-sensitive. In the paper, the viability of HWE reactions with lithium chloride under basic conditions was tested with bases such as potassium tert-butoxide and DBU.

(Figure 4)

Additional three papers related:

1.Citation:

Gant, T. G.; Meyers, A. Tetrahedron 1994, 50 (8), 2297–2360.

Blanchette’s paper on Horner-Wadsworth-Emmons reactions was cited in Gant’s “The chemistry of 2-oxazolines (1985–present)” for the production of molecule 257 from molecule 256 which uses the Horner-Wadsworth-Emmons reaction.

2.Citation:

Kolb, H. C.; Sharpless, K. Tetrahedron 1992, 48 (48), 10515–10530.

Blanchette’s paper on Horner-Wadsworth-Emmons reactions was cited in Kolb’s “A Simplified Procedure for the Stereospecific Transformation of 1,2-Diols into Epoxides” for the preparation of an unsaturated ester (molecule 5) from 2-(8-phenyloctyl)benzenecarbaldehyde by Wadsworth-Horner-Emmons olefination with trimetbyl phosphonoacetate under the reaction conditions described by the Roush modification.

3.Citation:

Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99 (6), 1549–1582.

This paper cited the Blanchette paper because they attempted to perform a HWE reaction under standard conditions with polymer-bound ketones, but they were unreactive, so they had to use a strong base. Their reagents were base sensitive, so they used lithium bromide, a lithium salt, as described in Blanchette’s paper.