Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(6): 0784-0788
DOI: 10.1055/s-2002-25775
DOI: 10.1055/s-2002-25775
PAPER
© Georg Thieme Verlag Stuttgart · New York
Iodine-Catalyzed, Efficient and Mild Procedure for Highly Chemoselective Acetalization of Carbonyl Compounds under Neutral Aprotic Conditions
Further Information
Received
2 January 2002
Publication Date:
26 April 2002 (online)
Publication History
Publication Date:
26 April 2002 (online)
Abstract
Various types of carbonyl compounds are efficiently converted to their 1,3-dioxanes by the use of 1,3-bis(trimethylsiloxy)propane (BTSP) and a catalytic amount of iodine (3-7 mol%) under essentially neutral aprotic condition.
Key words
carbonyl compounds - chemoselectivity - protection - 1,3-bis(trimethylsiloxy)propane - iodine
-
1a
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999. -
1b
Kocienski PJ. Protecting Groups Thieme; New York: 1994. -
2a For a review see:
Meskens AJ. Synthesis 1981, 501 -
2b For more recent leading references see:
Shibagaki M.Takahashi K.Kuno H.Matsushita H. Bull. Chem. Soc. Jpn. 1990, 63: 1258 -
2c
Ott J.Ramos Tombo GM.Schmid B.Venanzi LM.Wang G.Ward TR. Tetrahedron Lett. 1989, 30: 6151 -
2d
Otera J.Mizutani T.Nazaki H. Organometallics 1989, 8: 2063 -
2e
Ma S.Venanzi LM. Synlett 1993, 751 -
2f
Wang WB.Shi LL.Huang YZ. Tetrahedron Lett. 1990, 45: 3315 -
2g
Corla F.Venanzi LM. Helv. Chim. Acta 1993, 73: 690 -
2h
Fukuzawa S.Tsuchimoto T.Hotaka T.Hiyama T. Synlett 1995, 1077 ; and references cited therein -
2i
Tateiwa J.Horiuchi H.Uemura S. J. Org. Chem. 1995, 60: 4039 ; and references cited therein - 3
Seebach D.Imwinkelried R.Weber T. Modern Synthetic MethodsScheffold R. Springer Verlag; Berlin: 1986. p.125-259 -
4a
Tsunodu T.Suzuki M.Noyori R. Tetrahedron Lett. 1980, 21: 1357 -
4b
Hwu JR.Wetzel JM. J. Org. Chem. 1985, 50: 3946 -
4c
Hwu JR.Leu LC.Robl JA.Anderson DA.Wetzel JM. J. Org. Chem. 1987, 52: 188 -
4d
Karimi B.Ebrahimian GR.Seradj H. Org. Lett. 1999, 1: 1737 ; and references cited therein -
5a
Karimi B.Miri-Ashtiani A. Chem. Lett. 1999, 1199 -
5b
Karimi B.Seradj H. Synlett 2000, 641 -
5c
Karimi B.Seradj H.Ebrahimian GR. Synlett 1999, 1456 -
5d
Karimi B.Seradj H.Tabaei MH. Synlett 2000, 1798 -
5e
Firouzabadi H.Karimi B.Eslami S. Tetrahedron Lett. 1999, 40: 4055 -
5f
Firouzabadi H.Iranpoor N.Karimi B. Synthesis 1999, 58 -
5g
Karimi B.Seradj H. Synlett 2001, 519 - 6
Karimi B.Golshani B. J. Org. Chem. 2000, 65: 7228