Solution and Solid Phase Synthesis of Unusual a-Amino Acids From

5.1.4.1 Enzymatic Methods ................................................................................. 253
5.1.4.2 mnion Chemisiry (including piuctanr) ........................................... 254
5.1.4.3 Other Methods for the Synthcsis of /%Substituted Asparti? Acids .......... 258
5.2 Resuits and Discussion ........................................................................................... 262
5.2. t Methylation of Cbz-Asp(0Me)OBO ester 5.38: Optimization and
Determination of Diastereoselectivi fy ....................................................... 262
5.2.2 Addition of Other Alkylation Agents to Cbz-Asp(OMe)OBO 5.38 ................... 267
5.2.3 Addition of Hereroatorns to Cbz-Asp(0Me)OBO 5.38 .................................... 268
5.2.4 Deprotection ami HPLC Analysis of fisubstituted Asparrie Acids .................. 270
5.2.5 Discussion of the Stereochemistry of Addition to Cbz-Asp(0Me)OBO 5.38 . . 27 1
53 S v ...................................... ....................................................................... 275
5.4 Experimental ............................................................................................................ 276
5.5 References ................................................................................................................ 297
Chapter Six
Soiid Phase Synthesis of B-Hydroxy-PSubstituted-a-Aho Acids
6.1 Introduction .................................................................................................... 3 0 3
6.1.1 Solid-Phase Synthesis of a-Amino Acids ...................................................... 304
6.2 ResuJts and Discussion ............................................................................................ 310
6.2.1 Synthesis of Resin-Bod PHydroxy-mbstituted- a-Amino Acids .............. -311
6.3 Summary ................................................................................................................. 321
6.4 Experime ntal ............................................................................................................ 322
6.5 References ................................................................................................................ 332
Cbapter Seven
ConclWons and Suggestions for Future Research
7.1 Conclusions ............................................................................................................. 336
7.2 Suggestions for Future Research .......................................................................... 337
7.3 References ................................................................................................................ 341