Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from N-tert- Butanesulfinyl Aldimines
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1 Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from -tert- Butanesulfinyl Aldimines R BR 2 J. Am. Chem. Soc. 2008, 130, Melissa A. Beenen, Chihul An, and Jonathan A. Ellman rrent Literature: 5/31/08 David nold David Wipf Group Page 1 of 11 6/25/2008
2 Background: Early to Mid 1990 s Marked the Initial Investigations of Platinum Catalyzed Diboration of Alkynes R 1 R 2 + B B B 2 (cat) 2 3 mol% [(PPh 3 ) 2 Pt(C 2 4 )] toluene, 80 o C R 1 R 2 C 6 13 Me Me (3h) (33 h) (20 h) (3h) Mechanism: P B 2 (cat) 2 Pt P Pt P P -P B 2 (cat) 2 P Pt R 1 R 2 P Pt R 1 P Pt R 2 R 1 R 2 P Pt R 1 R 2 rganometallics 1996, 15, David Wipf Group Page 2 of 11 6/25/2008
3 Background: In 2000, the First Example of A Transition- Metal-Catalyzed Diboration of Aldimines to form α-amino Boronate Esters was Reported Mechanistic Insight: Reaction is proposed to be catalyzed by an in situ formed Pt(0) complex. B 2 (cat) 2 Pt(cod)Cl 2 L n Pt(0) Cl Limitations: Racemic synthesis of α-amino boronate esters Selective for diaryl aldimines, reaction is incompatible with aliphatic aldimines Selective -B deboration is problematic rg. Lett. 2000, 2, David Wipf Group Page 3 of 11 6/25/2008
4 Background: Movement from Platinum to Copper Catalysis Diboration of Aldehydes Synthesis of an (α-boroxy)benzylcopper complex. A competent precatalyst for aldehyde diboration reactions. + B B Pentane rt, 1h B 91% B Me R B 2 (pin) 2 (IP r) Generated in situ 1 20 mol % 1 1 eq B 2 (pin) 2 1 mol % 2 1 eq B 2 (pin) 2 Benzene, rt, 22 h F 3 C Benzene, rt, 24 h 90 % Conversion Precatalyst optimization and reaction scope. R 73% 86% 87% 94% 71% (ICy)t-Bu J. Am. Chem. Soc. 2006, 128, David Wipf Group Page 4 of 11 6/25/2008
5 Background: Mechanistic Insights into the (ICy)t-Bu Catalyzed Diboration of Aldehydes ' ' B 2 (pin) 2 ' '? rearrangement ' ' ' Me ' (pin)b Benzene, rt, 21h 81% ' ' ' ' = 2,4,6-Me 3 C 6 2 ' = 2,6-(i-Pr) 2 C 6 3 ot bserved J. Am. Chem. Soc. 2006, 128, David Wipf Group Page 5 of 11 6/25/2008
6 Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from -tert-butanesulfinyl Aldimines: Catalyst Screen and ptimization Reactions (ICy)t-Bu S + B 2 R 2 17 h BR 2 J. Am. Chem. Soc. 2008, 130, David Wipf Group Page 6 of 11 6/25/2008
7 Substrate Scope R S + B B 5 mol% (ICy)t-Bu Benzene, rt R Synthesis of aliphatic -sulfinyl-α-amino boronate esters. S S B( pin) B (pin) B( pin) B (pin) TB DPS B (pin) 74%, >98:2 dr 59%, >98:2 dr 81%, 97:3 dr 75%, 96:4 dr 75%, >99:1 dr Synthesis of aromatic -sulfinyl-α-amino boronate esters. Lower yields reflect an increased susceptibility of protodeborylation. Cl Me F 3 C 54%, 99:1 dr 61%, 99:1 dr 57%, >98:2 dr 66% Integrated Yield >95:5 dr David Wipf Group Page 7 of 11 6/25/2008
8 Rationale for the bserved Sense of Induction The sense of induction is consistent with an open transition state with the reagent delivered from the least hindered face. S L n R Closed Transition State (not observed) David Wipf Group Page 8 of 11 6/25/2008
9 α-amino Boronic Acids as Pharmacophores for Protease Inhibition: Bortezomib (Velcade) Bortezomib B() 2 Bortezomib is currently in clinical use for the treatment of cancers such as multiple myeloma and mantle cell lymphoma. Bortezomib is a potent and selective sernine protease inhibitor. Chem. Rev. 2007, 107, 687.; David Wipf Group Page 9 of 11 6/25/2008
10 Application of the Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters: Synthesis of Bortezomib B (pin) 4.0 M Cl:dioxane, Me, diox ane, rt 3 Cl 93% B (pin) + Ph 1. TB TU, i-p r 2 Et C 2 Cl 2, 0 o C, 7h M Cl:diox ane C 2 Cl 2, 0 o C -> rt Cl 3 Ph B (pin) + 1. TBTU, i-pr 2 E t C 2 Cl 2, 0 o C, 7h 2. ibub( ) 2, pentane, M e, 1 Cl (aq) B () 2 41% over 4 steps The authors demonstrate a concise asymmetric synthesis of bortezomib with a 30% yield over 6 steps. David Wipf Group Page 10 of 11 6/25/2008
11 Conclusion The authors have developed the first transition metal catalyzed asymmetric addition of boron to a carbon-heteroatom double bond. The utility of this methodology has been showcased by the asymmetric synthesis of the biologically active α-amino boronic acid: bortezomib. This methodology can be easily applied to the synthesis of new α-amino boronic acid-based protease inhibitors and allows for an alternate route to the generation of α-chiral-amino boronate esters. B() 2 David Wipf Group Page 11 of 11 6/25/2008
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