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. 2009;48(4):776-9.
doi: 10.1002/anie.200804244.

Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis

Vijaya Bhasker Gondi  1 , Koji Hagihara, Viresh H Rawal
Affiliations

Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis

Vijaya Bhasker Gondi et al. Angew Chem Int Ed Engl. 2009.
No abstract available

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Figures

Figure 1
Figure 1
Hydrogen-bond donor catalysts for asymmetric aldol reaction with acetyl phosphonate.
Figure 2
Figure 2
X-ray crystal structure of phosphonate aldol product 15g.[18]
Scheme 1
Scheme 1
Mukaiyama aldol reactions with pyruvonitrile.
See this image and copyright information in PMC

References

    1. Review on enzymatic methods: Kafarski P, Lecjzak B. J. Mol. Catal. B. 2004;29:99–104.

    1. Reviews on chemical methods: Wiemer DF. Tetrahedron. 1997;53:16609–16644. Gröger H, Hammer B. Chem. Eur. J. 2006;6:943–948.

    1. Kinetic resolution using enzymes: Li YF. Tetrahedron: Asymmetry. 1993;4:109–120. Khushi T, O’Toole KJ, Sime JT. Tetrahedron Lett. 1993;34:2375–2378. Drescher M, Li YF, Hammerschmidt F. Tetrahedron. 1995;51:4933–4946. Drescher M, Hammerschmidt F, Kahling H. Synthesis. 1995:1267–1272. Wuggenig F, Hammerschmidt F. Monatsh. Chem. 1998;129:423–436.

    1. Examples of asymmetric reduction using enzymes: Maly A, Lejczak B, Kafarski P. Tetrahedron: Asymmetry. 2003;14:1019–1024. and references therein.

    1. Reduction of keto phosphonates: Gajda T. Tetrahedron: Asymmetry. 1994;5:1965–1972. Meier C, Laux WHG. Tetrahedron: Asymmetry. 1996;7:89–94. Nesterov V, Kolodyazhnyi OI. Russ. J. Gen. Chem. 2005;75:1161–1162.

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