Organic chemists have always been fascinated by the cyclopropane subunit.1 The smallest cycloalkane is found as a basic structural element in a wide range of naturally occurring compounds.2 Moreover, many cyclopropane-containing unnatural products have been prepared to test the bonding features of this class of highly strained cycloalkanes3 and to study enzyme mechanism or inhibition.4 Cyclopropanes have also been used as versatile synthetic intermediates in the synthesis of more functionalized cycloalkanes5,6 and acyclic compounds.7 In recent years, most of the synthetic efforts have focused on the enantioselective synthesis of cyclopropanes.8 This has remained a challenge ever since it was found that the members of the pyrethroid class of compounds were effective insecticides.9 New and more efficient methods for the preparation of these entities in enantiomerically pure form are still evolving, and this review will focus mainly on the new methods that have appeared in the literature since 1989. It will elaborate on only three types of stereoselective cyclopropanation reactions from olefins: the halomethylmetal-mediated cyclopropanation reactions (eq 1), the transition metal-catalyzed decomposition of diazo compounds (eq 2), and the nucleophilic addition-ring closure sequence (eqs 3 and 4). These three processes will be examined in the context of diastereoand enantiocontrol. In the last section of the review, other methods commonly used to make chiral, nonracemic cyclopropanes will be briefly outlined.

Stereoselective Cyclopropanation Reactions

Chiral Allylic and Allenic Stannanes as Reagents for Asymmetric Synthesis

Pseudorotaxanes Formed Between Secondary Dialkylammonium Salts and Crown Ethers

Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

The formyl C–H⋯O hydrogen bond as a critical factor in enantioselective Lewis-acid catalyzed reactions of aldehydes

Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents

Remarkable increase in the diastereofacial selectivity of the addition of β-methyl α-(alkoxy)allylstannane to aldehydes: substituent effects on diastereofacial selectivity

The syn-CH 3 CHO-BF 3 complex is only 1.22 kcal mol -1 less stable than the corresponding anti-CH 3 CHO-BF 3 complex at the MP2/6-31G* level of theory. The corresponding difference in syn- and anti-PhCHO-BF 3 complexes is 5.31 kcal mol -1 . The calculated C-C=O (129 o ) and C-O-B (156 o ) angles for syn-PhCHO-BF 3 complexes have a much greater deviation from the standard geometries of a sp2 orbital than that (123.9 o and 125.4 o ) calculated for syn-CH 3 CHO-BF 3 complexes

A study of the electronic structures of boron trifluoride complexes with carbonyl compounds by ab initio MO methods

Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes

A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations. If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes. Furthermore, conformer I becomes preferred even for the γ-hydrory-α,β-unsaturated esters, which normally favor the CO-eclipsed form (II). On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the γ-hydroxy-α,β-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes

Conformational study of chiral alkenes: the influence of protective groups on the relative stability of ground-state rotational isomers

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