Asymmetric aldol reactions employing a cyclic sulfamide chiral auxiliary
Titanium-mediated aldol reactions using a C2 symmetric chiral auxiliary afforded syn dialdols with excellent stereoselection.
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Cited by (48)
Efficient synthesis of unsymmetrical sulfamides from sulfamic acid salts by activation with triphenylphosphine ditriflate
2019, TetrahedronCitation Excerpt :Owing to these applications, chemists have developed a few methods to access sulfamides. An efficient and operationally straightforward Mitsunobu reaction sequence furnishes unsymmetrical dialkyl sulfamides from primary or secondary alcohol precursors (Scheme 2A) [6]; however, access to dialkyl sulfamides from amines can be challenging. Some N,N′-dialkyl sulfamides can be prepared by sequential addition of two alkylamines to sulfuryl chloride (Scheme 2B) [7], a sulfuryldiimidazole analogue (Scheme 2C) [8], or catechol sulfate (not depicted) [9].
Cyclosulfamide as a chiral auxiliary: Application to efficient asymmetric synthesis (alkylation/aldolization)
2010, Tetrahedron AsymmetryCitation Excerpt :This new organization confers a gain of stability and rigidity to the transition state through the pseudo-chair ring involving both the chelated metal and the Pro-S sulfone oxygen. During the aldol reactions, the observation of our syn-aldol products suggests a chlorotitanium enolate proceeding through a Zimmerman–Traxler transition state,12 within which both the aldehyde and the cyclosulfamide are coordinated to titanium. This approach can be realized only by the most polar and the less hindranced Re-face.
Macrocyclic sulfamides: synthesis, hybridization, and metal binding properties
2008, Tetrahedron Letters