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. 2009 May 27;50(21):2464-2466.
doi: 10.1016/j.tetlet.2009.03.092.

Synthesis of Boc-protected bicycloproline

Sujeewa Ranatunga  1 , Juan R Del Valle
Affiliations

Synthesis of Boc-protected bicycloproline

Sujeewa Ranatunga et al. Tetrahedron Lett. .

Abstract

The synthesis of a highly constrained quaternary carbocyclic α-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring.

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Figures

Figure 1
Figure 1
General structures of some constrained α-amino acids.
Figure 2
Figure 2
Bicycloproline and related structures.
Scheme 1
Scheme 1
Synthesis of 4 (RSM = recovered starting material).
Scheme 2
Scheme 2
Selectivity of C–H insertion in related substrates.
Scheme 3
Scheme 3
Synthesis of aminoalcohol 17.
Scheme 4
Scheme 4
Synthesis and X-ray structure of (+)-N-Boc-bicycloproline (23).
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