Method for preparing .alpha.-chloroboronic acids from mannitol

Details Method for preparing .alpha.-chloroboronic acids from mannitol Method for preparing .alpha.-chloroboronic acids from mannitol

1997-07-07

1999-10-26

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Borate esters

558286, 558298, C07F 504

Patent

active

059731850

ABSTRACT:
A novel process for making compounds of Formula I, ##STR1## wherein X is a leaving group selected from the group Br, Cl, TsO, MsO, and TfO and R is a 1,2-diol, from a compound of Formula II: ##STR2## is described.

REFERENCES:
CA; 99; 21568 abs of Trimethuylsileniol as a leaving group in preparative organic chem, Vorbrueggen Curr. Trends in Org. Synthesis Conf. 4th Int.
J. Wityak, R. A. Earl, M.M. Abelman, Y.B. Bethel, B.N. Fisher, G.S. Kauffman, C.A. Kettner, P. Ma, J.L. McMillan, L.J. Mersinger, J. Pesti, M.E. Pierce, F.W. Rankin, R.J. Chorvat and P.N. Confalone, J. Org. Chem. 1995, 60(12), 3717-3722, "Synthesis of Thrombin Inhibitor DuP 714".
R.W. Hoffmann and S. Dresely, Synthesis 1988, 103-105, "Preparation of 3-Substituted (E)-1-Alkenylboronic Esters".
R.W. Hoffmann and S. Dresely, Agnew. Chem. Int. Ed. Engl. 1986, 25(2), 189-190, "Optically Active .alpha.-Cloro-(E)-crotylboronate Esters by Allyl Rearrangement".
D.S. Matteson and K.M. Sadhu, J. Am. Chem. Soc. 1981, 103, 5241-5242, "(R)-1-Acetamido-2-phenylethanebornic Acid. A Specific Transition-State Analogue for Chymotrypsin".
B. Jiang and P. Ma, Synthetic Communications, 1995, 25(22), 3641-3645, "An Improved Synthesis of (+)-3,4--Isopropylidene Butyne".
R.W. Hoffmann, S. Dresely and J.W. Lanz, Chem. Ber. 1988, 121, 1501-1507, "Addition of (.alpha.-Chlorocrotyl)boronates to aldehydes".
D.S. Matteson, Chem. Rev. 1989, 89, 1535-1551, ".alpha.-Halo Boronic Esters: Intermediates for Stereodirected Synthesis".

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