Highly Efficient Transthioacetalization of O,O-Acetals Catalyzed by Indium(III) Chloride

Brindaban C. Ranu; Arijit Das; Sampak Samanta

doi:10.1055/s-2002-25347

LETTER

Highly Efficient Transthioacetalization of O,O-Acetals Catalyzed by Indium(III) Chloride

Brindaban C. Ranu*, Arijit Das, Sampak Samanta
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta - 700 032, India
Fax: +91(33)4732805; e-Mail: ocbcr@mahendra.iacs.res.in;

Abstract

All articles of this category

Abstract

A simple, efficient and general procedure has been developed for the transthioacetalization of O,O-acetals catalyzed by indium(III) chloride in 1,2-dichloroethane.

Key words

transthioacetalization - indium(III) chloride - O,O-acetals - S,S-thioacetals

Full Text

References

<A NAME="RG00402ST-1A">1a</A> Oriyama T. Oda M. Gono J. Koga G. Tetrahedron Lett. 1994, 35: 2027

<A NAME="RG00402ST-1B">1b</A> Yang G. Ding X. Kong F. Tetrahedron Lett. 1997, 38: 6725

<A NAME="RG00402ST-1C">1c</A> Oriyama T. Kimura M. Koga G. Bull. Chem. Soc. Jpn. 1994, 67: 885

<A NAME="RG00402ST-1D">1d</A> Oriyama T. Yatabe K. Sugauttra S. Machiguchi Y. Koga G. Synlett 1996, 523

<A NAME="RG00402ST-1E">1e</A> Ranu BC. Hajra A. J. Chem. Soc., Perkin Trans. 1 2001, 2262

<A NAME="RG00402ST-2">2</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999.

<A NAME="RG00402ST-3A">3a</A> Corey EJ. Seebach D. Angew. Chem., Int. Ed. Engl. 1965, 4: 1075

<A NAME="RG00402ST-3B">3b</A> Corey EJ. Seebach D. Angew. Chem., Int. Ed. Engl. 1965, 4: 1077

<A NAME="RG00402ST-3C">3c</A> Seebach D. Angew. Chem., Int. Ed. Engl. 1969, 8: 639

<A NAME="RG00402ST-3D">3d</A> Grobal BT. Seebach D. Synthesis 1977, 357

<A NAME="RG00402ST-4">4</A> Pettit GR. Van Tamelen EE. Org. React. 1962, 12: 356

<A NAME="RG00402ST-5A">5a</A> Park JH. Kim S. Chem. Lett. 1989, 629

<A NAME="RG00402ST-5B">5b</A> Tani H. Masumoto K. Inamasu T. Tetrahedron Lett. 1991, 32: 2039

<A NAME="RG00402ST-5C">5c</A> Saraswathy VG. Sankaraman S. J. Org. Chem. 1994, 59: 4665

<A NAME="RG00402ST-5D">5d</A> Firouzabadi H. Iranpoor N. Karimi B. Synlett 1998, 739

<A NAME="RG00402ST-5E">5e</A> Firouzabadi H. Iranpoor N. Karimi B. Synlett 1999, 319

<A NAME="RG00402ST-5F">5f</A> Firouzabadi H. Iranpoor N. Karimi B. Hazarkhani H. Synlett 2000, 263

<A NAME="RG00402ST-5G">5g</A> Firouzabadi H. Iranpoor N. Hazarkhani H. Synlett 2001, 1641

<A NAME="RG00402ST-6">6</A> Firouzabadi H. Iranpoor N. Hazarkhani H. J. Org. Chem. 2001, 66: 7527

<A NAME="RG00402ST-7A">7a</A> Li C.-J. Chan T.-H. Tetrahedron 1999, 55: 11149

<A NAME="RG00402ST-7B">7b</A> Chauhan KK. Frost CG. J. Chem. Soc., Perkin Trans. 1 2000, 3015

<A NAME="RG00402ST-7C">7c</A> Ghosh R. Indian J. Chem. Sect. B 2001, 40B: 550

<A NAME="RG00402ST-7D">7d</A> Yadav JS. Abraham S. Reddy BVS. Sabitha G. Tetrahedron Lett. 2001, 42: 8063

<A NAME="RG00402ST-7E">7e</A> Loh T.-P. Feng L.-C. Wei L.-L. Tetrahedron 2001, 57: 4231

<A NAME="RG00402ST-7F">7f</A> Yang X.-F. Mague JT. Li C.-J. J. Org. Chem. 2001, 66: 739

<A NAME="RG00402ST-8A">8a</A> Ranu BC. Jana U. J. Org. Chem. 1998, 63: 8212

<A NAME="RG00402ST-8B">8b</A> Ranu BC. Hajra A. Jana U. Org. Lett. 1999, 1: 1141

<A NAME="RG00402ST-8C">8c</A> Ranu BC. Hajra A. Jana U. Tetrahedron Lett. 2000, 41: 531

<A NAME="RG00402ST-8D">8d</A> Ranu BC. Hajra A. Jana U. J. Org. Chem. 2000, 65: 6270