Aldol Reactions by Rainer Mahrwald

By Rainer Mahrwald

Aldol Reactions offers a complete up to date evaluate of aldol reactions together with software of other steel enolates; catalytic aldol additions catalyzed by way of varied Lewis acids and Lewis bases; enantioselective direct aldol additions; antibodies and enzyme catalyzed aldol additions and the hot competitive improvement of organocatalyzed aldol additions. the facility of every technique is validated by way of a number of purposes in overall synthesis of typical items. the professionals and cons of those methodologies with reference to stereoselectivity, regioselectivity and alertness in overall synthesis of common items are mentioned. nice value is decided to the varied chances of the guide of aldol response to put in required configurations in advanced normal product synthesis.

Quality: Vector, Searchable, Bookmarked

Show description

Read or Download Aldol Reactions PDF

Similar organic chemistry books

Metal-catalized cross-coupling reactions

Carbon-carbon bond forming reactions are arguably an important strategies in chemistry, as they signify key steps within the construction of advanced molecules from basic precursors. between those reactions, metal-catalyzed cross-coupling reactions are widely hired in quite a lot of parts of preparative natural chemistry, starting from the synthesis of advanced typical items, to supramolecular chemistry, and fabrics technology.

Odour Prevention and Control of Organic Sludge and Livestock

Lawsuits of a round-table seminar, Silsoe, united kingdom, 15-19 April 1985.

Extra resources for Aldol Reactions

Sample text

Abiko A (2002) Org Synth 79:103 19. Brown HC, Ganesan K, Dhar R (1993) J Org Chem 58:147 20. Chow HF, Seebach D (1986) Helv Chim Acta 69:604 21. Hirama M, Masamune S (1979) Tetrahedron Lett 2225 22. Evans DA, Nelson JV, Vogel E, Taber TR (1981) J Am Chem Soc 103:3099 23. Hirama M, Garvey DS, Lu LDL, Masamune S (1979) Tetrahedron Lett 20:937 24. Cergol KM, Coster MJ (2007) Nature Protocols 2:2568 25. Abiko A, Liu JF, Masamune S (1996) J Org Chem 61:2590 26. Evans DA, Bartroli J (1982) Tetrahedron Lett 23:807 27.

7,8,9 After these initial reports the attention was drawn to the stereoselective execution of this method. The aldol addition proceeds via a chair-like, six-membered transition state, which is more rigid than those of alkali metal enolates. This is due to the shorter boron oxygen bond length, which guarantees a maximum of 1,3-diaxial interactions (R3 ↔ L) and thus the formation of the more stable transition states A and B. For that reason higher stereoselectivities were observed when used with boron enolates, compared to aldol additions of corresponding lithium enolates.

4 Titanium Enolates Titanium enolate-based aldol additions have a tremendous synthetic potential. 3 The titanium enolates were generated mostly by transmetallation of corresponding lithium enolates with ClTi(Oi-Pr)3 or ClTi(NR2)3. 1). 1. LDA O 2. Ti(Oi-Pr)3Cl O 3. 4 Evans and coworkers used a combination of TiCl4 and i-Pr2NEt for syn-selective aldol addition. 5 For results with (S)-2-benzyloxy-3-pentanone in aldol additions under these conditions see Rodriguez-Cisterna et al. 6,7 R. V. 8 1. TiCl4, amine O 2.

Download PDF sample

Rated 4.06 of 5 – based on 19 votes